3-Methyl-3-hydroxy-2-butanone

To illustrate the concept, Figure 6.16 shows the expected results of a normal 13C spectrum and an APT spectrum of 4-hydroxy-3-methyl-2-butanone. The APT spectrum shows all carbons including the quaternary C=0 and solvent carbons, and sorts the carbons into categories of CH and CH3 ( up peaks) and quaternary and CH2 ( down peaks). Note that sometimes APT spectra are presented upside down with CH and CH3 peaks down and quaternary and CH2 peaks up , but the deuterated solvent peak (no attached protons) tells us how to interpret it. 

Thus an almost quantitative yield of ethyl l-(hydroxymethyl)-2-oxocyclo-hexanecarboxylate is obtained from ethyl 2-oxocyclohexanecarboxylate and aqueous formaldehyde in the presence of calcium oxide 687 and 2-butanone and formaldehyde in sodium hydroxide solution give a 70% yield of 4-hydroxy-3-methyl-2-butanone, whence 3-methyl-3-buten-2-one is formed in 74% yield by removal of water.688 Hydroxymethylation of acetone689 and of co-nitrotoluene (phenylnitromethane)690 have also been reported. 

C5H10O2, 4-Hydroxy-3-methyl-2-butanone, CH3C(0)CH(CH3)CH20H OH, 696 NO3, 699 AF, 698... 

Methyl vinyl ketone can be produced by the reactions of acetone and formaldehyde to form 4-hydroxy-2-butanone, followed by dehydration to the product (267,268). Methyl vinyl ketone can also be produced by the Mannich reaction of acetone, formaldehyde, and diethylamine (269). Preparation via the oxidation of saturated alcohols or ketones such as 2-butanol and methyl ethyl ketone is also known (270), and older patents report the synthesis of methyl vinyl ketone by the hydration of vinylacetylene (271,272). 

Biacetyl is produced by the dehydrogenation of 2,3-butanediol with a copper catalyst (290,291). Prior to the availabiUty of 2,3-butanediol, biacetyl was prepared by the nitrosation of methyl ethyl ketone and the hydrolysis of the resultant oxime. Other commercial routes include passing vinylacetylene into a solution of mercuric sulfate in sulfuric acid and decomposing the insoluble product with dilute hydrochloric acid (292), by the reaction of acetal with formaldehyde (293), by the acid-cataly2ed condensation of 1-hydroxyacetone with formaldehyde (294), and by fermentation of lactic acid bacterium (295—297). Acetoin [513-86-0] (3-hydroxy-2-butanone) is also coproduced in lactic acid fermentation. 

Pentanol in fraction 2 and to 61% for 3-Methyl-3-Hydroxy-2-Butanone in fraction 3. 

Raspberry ketone is prepared by alkali-catalyzed condensation of the alkali salt of 4-hydroxybenzaldehyde and acetone, followed by selective hydrogenation of the double bond in the resulting 4-hydroxybenzalacetone. Other syntheses start from phenol which is converted into 4-(4-hydroxyphenyl)-2-butanone with methyl vinyl ketone (e.g., in the presence of phosphoric acid) [179] or with 4-hydroxy-2-butanone in the presence of concentrated sulfuric acid [180]. 

SCHEME 9. 2-Hydroxypropanal (19), 3-hydroxy-2-butanone 20 and 3,4-di-0-methyl-TO-(tri-methylsilyl)-L-erythmlose (21), used as the carbonyl substrate in 17... 

Reaction of anthranilonitrile or methyl anthranilate with 3-hydroxy-2-butanone followed by malononitrile gave the pyrrolo [1,2-a] quinazoline 16 (79AP552). Both of the diazine and azole rings of pyrroloquinazolines were also simultaneously formed by cyclization of the anilide 17 derived from 3-chloropropionic acid and 2-aminobenzophenone with potassium cyanide to afford the pyrrolo [1,2-a] quinazoline 18 (68JHC185 71USP3595861). 

Methyl ketones from esters (12, 126).1 The reaction of a carboxylic acid or ester with CH3Li and ClSi(CH3)3 to provide a methyl ketone has been used to obtain a silyl protected (S)-3-hydroxy-2-butanone (2) from ethyl lactate (1). The addition of... 

Hydroxy-2-butanone and its methyl ether were also hydrogenated in 69 and 68% ee, respectively, using the same modified nickel catalyst.211 Acetylacetone was first hydrogenated to (R)-4-hydroxy-2-pentanone in 87% ee over the Raney Ni modified by (R,R)-tartaric acid. Then the (R)-hydroxy ketone was hydrogenated to a mixture of... 

Acetoin FEMA No. 2008 Acetyl Methyl Carbinol Dimethylketol 3-Hydroxy-2-butanone Monomer 88.n/c4H802/ CH3CH(OH)COCH3 Monomer colorless to pale yel liq/ buttery Monomer m—ale, prop glycol, water ins—veg oils/ 148° ... 

SYNS ACETYL METHYL CARBINOL 2-BUTAN-OI 3-ONE 2,3-BUTANOLONE DIMETHYL-KETOL FEMA No. 2008 3-HYDROXY-2-BUTANONE 1-HYDROXYETHYL METHYL KETONE y-HYDROXY-P-OXOBUTANE... 

C4H802 (R)-3-hydroxy-2-butanone 53584-56-8 416.20 35.894 1,2 3627 C4H9CIO 3-chloro-2-methyl-1-propanol 10317-10-9 388.26 33.261 2... 

Figure 5.2.10. Cellulose pyrolysate obtained at 59CP C by Py-GC/MS. The separation was done on a Carbowax type column. 1 CO2, 2 acetaldehyde, 3 acetone, 4 2-butanone, 5 2,3-butandione, 6 toluene, 7 water, 8 cyclopentanone, 9 methylfuran, 10 3-hydroxy-2-butanone, 11 hydroxypropanone, 12 cyclopent-1-en-2-one, 13 2-methylcyclopentenone, 14 acetic acid, 15 acetic acid anhydride, 16 furancarboxaldehyde, 17 methylcyclopentenone, 18 dimethylcyclopentenone, 19 5-methylfurancarboxaldehyde, 20 2,3-dihydro-2-furanone, 21 furan-2-methanol, 22 3-methylfuran-2-one, 23 2(5H)-furanone, 24 hydroxycyclopentenone, 25 3,5-dimethylcyclopentan-1,2-dione, 26 2-hydroxy-3-methyl-2-cyclopenten-1-one, 27 2-hydroxy-3-ethyl-2-cyclopenten-1-one, 28 2,3-dimethyl-2-cyclopenten-1-one, 29 phenol, 30 dimethylphenol, 31 3 thyl-2,4(3H,5H)-furandione, 32 3-butenoic acid, 33 1,4 3,6-dianhydro-a-D-glucopyranose, 34 5-(hydroxymethyl)-furfural.

Zimmermann and Eger treated methyl anthranilate and anthraniloni-trile first with 3-hydroxy-2-butanone in toluene, in the presence of a catalytic... 

CIC The powerful odour is dominated by 2-isobutyl thiazole and 3-pentanethiol. The green notes are lipid degradation products like (E)-2-hexenal, hexanal and higher unsaturated aldehydes, the pineapple-pear like fruity notes are derived from methyl hexanoate, ethyl-2-hexenoate and hexyl acetate. The spicy cinnamon notes are represented by 3-phenyl propyl acetate, cinnamyl acetate, methyl cinnamate, ethyl cinna-mate and ciimamaldehyde. Gamma-decalactone and 2,5-dimethyl-4-hydroxy-furan-3(2H)-one and 3-hydroxy-2-butanone add the sweet, creamy body. Beta-famesene, citronellol, 2-phenylethanol, beta-ionone add the sweet, floral, quincelike part and methyl benzoate and ethyl benzoate impart a characteristic medicinal, exotic topnote. 

Since the enolization is not restricted to the 2 and 3 positions, a number of products are formed that undergo subsequent aldol condensations and the Cannizzaro oxidation. They are all 2-hydroxy-3-methyl, 3,4-dimethyl-2-hydroxy, 3,5-dimethyl-2-hydroxy, and 3-ethyl-2-hydroxy-2-cyclopenten-l-ones sugar acids acetic acid hydroxyacetone three isomeric hydroxy-2-butanones y-butyrolactone and such furan derivatives as furyl alcohol, 5-methyl-2-furyl alcohol, and 2,5-dimethyl-4-hydroxy-3(2H)-furanone. They are food flavoring agents. 

The application range of modified Raney Ni has been extended to the enantio-selective hydrogenation of other -functionalized ketones such as y0-diketones (e. g. acetylacetone, 74% ee), 4-hydroxy-2-butanone and its methyl ether (68-70% ee), and ff-ketosulfones (67-71 % ee) [11]. 

Acetyl methyl carbinol CAS 513-86-0 EINECS/ELINCS 208-174-1 UN 2621 (DOT) FEMA 2008 Synonyms Acetoin 2,3-Butanolone 2-Butanol-3-one Dimethylketol 3-Hydroxy-2-butanone 1-Hydroxyethyl methyl ketone y-Hydroxy-p-oxobutane... 

Preparation of 3-Methyl-3-hydroxy-2-butanone, p. 412 Hydrolysis of Anhydrides, p. 432... 

Scheme 23 also outlines a potential problem with the syjnthesis. The initial attack can occur at either end of the double bond of the 7r-complex, 28, to give the two isomers 29 and 30 in a ratio of 4 1. These two isomers are expected from Wacker chemistry since propene produces both acetone and propanal in about the same ratio from the two modes of addition. However, as shall be discussed below, this is not a serious problem with most a-olefins. The same catalyst oxidizes methyl vinylketone only to 4-chloro-3-hydroxy-2-butanone (29 R = C(=0)CH3). The optical purity was still only about 12%. 

Goodwin and Treble (78a) have reported that the addition of 3-hydroxy-2-butanone-l-C to growing cultures of E. ashbyii led to incorporation of radioactivity into ring A of riboflavin exclusively. One-half of the was in the methyl groups and none in carbons 6 and 7 of the o-xylene moiety. The labeled acetoin was incorporated more effectively than acetate-2-Cn into ring A. 

---