Acetic butyl ester

Least toxic of the four isomers of acetic butyl ester vapors irritant to eyes and respiratory tract narcotic at high concentrations TLV-TWA air 200 ppm (—950 mg/m ) (ACGIH,... 

So-called pure acryUc latexes are employed for maximum durabiUty as required, for example, in high performance exterior latex paints. On the other hand, interior flat wall latex paints do not need the high resistance to exterior exposure and hydrolysis. The most widely used latexes for this appHcation are vinyl acetate copolymer latexes such as vinyl acetate/butyl acrylate (2-propenoic acid butyl ester) [141-32-2] copolymers having just sufficient... 

Unsaturated Hydrocarbons. Olefins from ethylene through octene have been converted into esters via acid-catalyzed nucleophilic addition. With ethylene and propjiene, only a single ester is produced using acetic acid, ethyl acetate and isopropyl acetate, respectively. With the butylenes, two products are possible j -butyl esters result from 1- and 2-butylenes, whereas tert-huty esters are obtained from isobutjiene. The C5 olefins give rise to three j iC-amyl esters and one /-amyl ester. As the carbon chain is lengthened, the reactivity of the olefin with organic acids increases. 

Me2Sn(SMe)2, BF3-Et20, PhCH3, 0°, 3-24 Ji AcOH, 75-100% yield." An ethyl ester can be hydrolyzed in the presence of an MEC ester with 1 N aqueous NaOH-DMSO (1 1), and MEC esters can be cleaved in the presence of ethyl, benzyl, cinnamyl, and t-butyl esters as well as the acetate, TBDMS and MEM ethers. 

The TCBOC group is stable to the alkaline hydrolysis of methyl esters and to the acidic hydrolysis of r-butyl esters. It is rapidly cleaved by the supemucleophile lithium cobalt(I)phthalocyanine, by zinc in acetic acid, and by cobalt phthalocy-anine (0.1 eq., NaBH4, EtOH, 77-90% yield). 

Acetate Esters Methyl acetate Ethyl acetate Propyl acetate Isopropyl acetate Butyl acetate Isobutyl acetate Amyl acetate... 

Chemical Designations - Synonyms Acetic Acid, Butyl Ester Butyl Acetate Butyl Ethanoate Chemical Formula CH3COO(CHj)3CH3... 

Chemical Designations - Syrumyms Acetic Acid, sec-Butyl Ester Chemical Formula CH3C00CH(CH3)CH3CH3. 

Alkali metal alkoxides, r-butyl acetate neat, 45°, 30 min, 98% yield of r-butyl ester from methyl benzoate. The rate constant for the reaction increases with increasing ionic radius of the metal and with decreasing polarity of the solvent. Equilibrium for the reaction is achieved in <10 sec. Other examples eire presented. " ... 

Benzyltriethylammonium tetrathiomolybdate in CH3CN in 61-97% yield. Deprotection is compatible with esters such as benzyl, allyl, acetate, and -butyl esters. ... 

The next step yields 1-(3-acetylthio-2-methylpropanoyl)-L-proline tert-butyl ester. L-proline tert-butyl ester (5.1 g) is dissolved in dichloromethane (40 ml) and the solution stirred and chilled in an ice bath. Dicyclohexylcarbodiimide (15 ml) is added followed immediately by a solution of 3-acetylthio-2-methylpropanoic acid (4.9 g) in dichloromethane (5 ml). After 15 minutes stirring in the ice bath and 16 hours at room temperature, the precipitate is filtered off and the filtrate is concentrated to dryness in vacuo. The residue is dissolved in ethyl acetate and washed neutral. The organic phase is dried over magnesium suifateand concentrated to dryness in vacuo. The residue 1-(3-acetylthio-2-methylpropanoyl)-L-proline tert-butyl ester is purified by column chromatography (silica gel-chloroform), yield 7.9 g. 

Then, 1-(3-acetylthio-2-methylpropanoyl)-L-proline is produced. The 1-(3-acetylthio-3-methyl-propanoyl)-L-proline tert-butyl ester (7.8 g) is dissolved in a mixture of anisole (55 ml) and trifluoroacetic acid (110 ml). After one hour storage at room temperature the solvent Is removed in vacuo and the residue is precipitated several times from ether-hexane. The residue (6.8 g) is dissolved in acetonitrile (40 ml) and dicyclohexylamine (4.5 ml) is added. The crystalline salt is boiled with fresh acetonitrile (100 ml), chilled to room temperature and filtered, yield 3 g, MP 187°C to 188°C. This material is recrystallized from isopropanol [ttlo -67° (C 1.4, EtOH). The crystalline dicyclohexylamine salt is suspended in a mixture of 5% aqueous potassium bisulfate and ethyl acetate. The organic phase is washed with water and concentrated to dryness. The residue is crystallized from ethyl acetate-hexane to yield the 1-(3-acetylthio-2-D-methylpropanoyl-L-proline, MP83°Cto 85°C. 

Likewise, synthetic 2//-azepines isomerize to 3//-azepines in refluxing chloroform (2-3 h) or in tert-butyl methyl ether at room temperature.291 The isomers can be readily separated by chromatography on silica gel, as the more basic 2//-azepines30 have lower Rf values. In contrast, 7-butyl-2//-azepin-2-acetic acid (11), obtained by heating the tert-butyl ester 10 with iodotrimethylsilane, is stabilized by intramolecular hydrogen bonding and shows no tendency to rearrange to the 3//-isomer.291... 

Acetic acid, butyryl-, ethyl ester [Hexanoic acid, 3-oxo-, ethyl ester] 55, 73, 75 Acetic acid, chloro-, tert-butyl ester [Acetic acid, chloro- 1,1-dimethylethyl ester], 55,94... 

In the presence of a strong base, the ot carbon of a carboxylic ester can condense with the carbonyl carbon of an aldehyde or ketone to give a P-hydroxy ester, which may or may not be dehydrated to the a,P-unsaturated ester. This reaction is sometimes called the Claisen reaction,an unfortunate usage since that name is more firmly connected to 10-118. In a modem example of how the reaction is used, addition of tert-butyl acetate to LDA in hexane at -78°C gives the lithium salt of ferf-butyl acetate, " (12-21) an enolate anion. Subsequent reaction a ketone provides a simple rapid alternative to the Reformatsky reaction (16-31) as a means of preparing P-hydroxy erf-butyl esters. It is also possible for the a carbon of an aldehyde or ketone to add to the carbonyl carbon of a carboxylic ester, but this is a different reaction (10-119) involving nucleophilic substitution and not addition to a C=0 bond. It can, however, be a side reaction if the aldehyde or ketone has an a hydrogen. 

Isobutyl chloroformate Formic acid, chloro-, isobutyl ester (8) Carbonochloridic acid, isobutyl ester (9) (543-27-1) S-tcrf-Butyl-L-cysteine ferf-butyl ester L-Cysteine, S-(l,l-dim-ethylethyl), 1,1-dimethylethyl ester (9) ( —) acetate (38024-19-0) hydrochloride (2481-11-0)... 

The application of 3-aminopropyl phosphine (3) [41,46] as a building block for incorporation into -COOH functionalized frameworks provides an excellent example of the utility of preformed primary phosphine frameworks (Scheme 8) [46]. The reactions involved Michael addition of ferf-butyl acrylate to malonic acid dimethyl ester to produce the intermediate adduct, 2-methoxycarbonyl-pentanedioc acid 5-ferf-butyl ester 1-methyl ester, which upon treatment with trifluro-acetic acid (TFA) produced the corresponding diester acid,2-methoxy-carbonyl-pentanedioic acid 1-methyl ester, in near quantitative yield. It is remarkable to note that the reaction of NH2(CH2)3PH2 (3) with the diester acid is highly selective as the -COOH group remained unattacked whereas the reaction occurred smoothly and selectively at the -COOMe groups to pro-... 

Several biphenylphosphines with 2 -amino substituents are also effective in arylation of ester enolates.174 Among the esters that were successfully arylated were f-butyl acetate, /-butyl propanoate, and ethyl phenylacetate. The ester enolates were generated with LiHMDS. 

The most frequently encountered hydrolysis reaction in drug instability is that of the ester, but curtain esters can be stable for many years when properly formulated. Substituents can have a dramatic effect on reaction rates. For example, the tert-butyl ester of acetic acid is about 120 times more stable than the methyl ester, which, in turn, is approximately 60 times more stable than the vinyl analog [16]. Structure-reactivity relationships are dealt with in the discipline of physical organic chemistry. Substituent groups may exert electronic (inductive and resonance), steric, and/or hydrogen-bonding effects that can drastically affect the stability of compounds. A detailed treatment of substituent effects can be found in a review by Hansch et al. [17] and in the classical reference text by Hammett [18]. 

Enantioselective allylations of a-nitro ketones and a-nitro esters with allyl acetates are carried out in the presence of 2 equiv of alkali metal fluorides (KF, RbF, CsF) and 1 mol% palladium catalysts prepared in situ from Pd2(dba)3-CHC13 and chiral phosphine ligands. Moderate enantio-selectivity (ca 50% ee) is reported for allylation of cx-nitroketones (Eq. 5.60). The highest selectivity (80% ee) is observed for allylation of the reaction of tert-butyl ester (Eq. 5.61).93... 

Macke recently introduced a monoreactive DOTA prochelator (4,7,10-tricarboxymethyl-tert-butyl ester A, A, A", A "-tetraazacyclododecane-1 -acetate), which was coupled to Tyr3—Lys5 (BOQ-octreotide via solid-phase peptide synthesis. A one-step deprotection reaction generated the bioactive compound DOTATOC in about 65% yield.142 The 90Y and 177Lu DOTATOC complexes have shown promise for the treatment of neuroendocrine tumors in early clinical trials.143,444... 

Bromo-N-Boc-glycine-tert-butyl ester Acetic acid, bromo[[(1,1-dimethylethoxy)-carbonyl]amino]-, 1,1-dimethylethyl ester, (+)-, (12) (111652-22-3) N-Boc-Glydne-tert-butyl ester Glycine, N-[(1,1-dimethylethoxy)carbonyl)-, 1,1-dimethylethyl ester (12) (111652-20-1)... 

Acetic acid, butyl ester Acetic acid, pentyl ester Acetic acid, decyl ester Acetic acid, benzyl ester Acetic acid, benzyl ester Acetic acid, 1-cyclohexenyl ester Acetic acid, 3-cyclohexenyl ester Butyric acid, benzyl ester Phenylacetic acid, propyl ester Oleic acid, methyl ester Linoleic acid, methyl ester Linolenic acid, methyl ester Adipic acid, methyl ester Adipic acid, ethyl ester Adipic acid, diethyl ester Adipic acid, dipropyl ester Adipic acid, (methylethyl)ester Adipic acid,... 

Glyoxal-sodium bisulfite, 30, 86 Glyoxylic acid, w-butyl ester, 35, 18 ethyl ester, diethyl acetal, 35, 59 Grignard reaction, addition to ethyl sec-butylidenecyanoacetate, 35, 7 allylmagnesium bromide with of,(3-di-bromoethyl ethyl ether, 36, 61 allylmagnesium chloride with a,/3-di-bromoethyl ethyl ether, 36, 63 ethylmagnesium bromide with tin tetrachloride, 36, 86... 

BUTYL DIAZOACETATE (Acetic acid, diazo-, fert-butyl ester)... 

FORMATION AND PHOTOCHEMICAL WOLFF REARRANGEMENT OF CYCLIC a-DIAZO KETONES D-NORANDROST-5-EN-3 -0L-16-CARB0XYLIC ACIDS, 52, 53 FORMIC ACID, AZIDO—, tert-BUTYL ESTER, 50, 9 Formylation, with acetic formic anhydride, 50, 2 p-FORMYLBENZENESULFONAMIDE, ... 

Uses Preparation of butyl esters (e.g., butyl acetate, di-n-butyl phthalate), glycol ethers solvent for waxes, resins, gums, and varnishes hydraulic fluid ingredient in perfumes and flavors additive in deicing fluids polishes, floor cleaners, stain removers, and in some gasolines (antiicing) diluent for brake fluids humectant for cellulose nitrate. 

Synonyms Acetic acid, butyl ester 1-Acetoxybutane AI3-00406 BRN 1741921 BuAc 1-Butanol acetate Butyl acetate 1-Butyl acetate /j-Butyl acetate Butyl ethanoate /j-Butyl ethanoate CCRIS 2287 EINECS 204-658-1 NSC 9298 UN 1123. 

Synonyms Acetic acid, 2-butoxy ester Acetic acid, sec-butyl ester Acetic acid, 1-methylpropyl ester BRN 1720689 2-BuAc sec-BuAc 2-Butanol acetate sec-Butanol acetate 2-Butanol ethanoate 2-Butyl acetate sec-Butyl alcohol acetate sec-Butyl ethanoate EINECS 203-300-1 Ethanoic acid, 1-methylpropyl ester 1-Methylpropyl acetate 1-Methylpropyl ethanoate NSC 8034 UN 1123. 

Synonyms Acetic acid, tert-butyl ester Acetic acid, 1,1-dimethylethyl ester BRN 1699506 t-BuAc 1-Butyl acetate lerl/arj-Butyl acetate 1-Butyl ethanoate tertiary-B Ay ethanoate 1,1-Dimethyl acetate 1,1-Dimethyl ethanoate EINECS 208-760-7 Ethanoic acid, lerl-butylbutyl ester Ethanoic acid, 1,1-dimethylethyl ester NSC 59719 TBAC Texaco lead appreciator TLA UN 1123. 

Acetamidofluorene, see 2-Acetylaminofluorene 2-Acetaminofluorene, see 2-Acetylaminofluorene Acetanhydride, see Acetic anhydride Acetasol, see Acetic acid Acetdimethylamide, see A,A-Dimethylacetamide Acetic acid, amyl ester, see Amyl acetate Acetic acid anhydride, see Acetic anhydride Acetic acid (aqueous soln), see Acetic acid Acetic acid, 2-butoxy ester, see sec-Butyl acetate Acetic acid, butyl ester, see Butyl acetate Acetic acid, sec-butyl ester, see sec-Butyl acetate Acetic acid, ferf-butyl ester, see ferf-Butyl acetate Acetic acid dimethylamide, see A,A-Dimethylacetamide Acetic acid, 1,3-dimethylbutyl ester, see sec-Hexyl acetate Acetic acid, 1,1-dimethylethyl ester, see ferf-Butyl acetate Acetic acid, ethenyl ester, see Vinyl acetate... 

Ethanoic acid, tert-butyl ester, see ferf-Bntyl acetate... 

Alkanes pentane, hexane, heptane, cyclohexane Chlorinated solvents chloroform, dichloromethane, 1,2-dichloroethane Ethers diethyl ether, methyl-t-butyl ether, diisopropyl ether Esters ethyl acetate, butyl acetate Long-chain alcohols butanol, octanol Aromatics benzene, toluene, xylene Alkanes pentane, hexane, heptane, cyclohexane Diethyl ether... 

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