Methyl chloroacetate acetate

B. Reactions.—(/) Halides. Whereas ylides are alkylated in the normal way on treatment with a-bromo- or a-iodo-esters, quite different reactions occur with a-fluoro- and a-chloro-acetates. When salt-free ylides were refluxed in benzene with ethyl fluoroacetate or trifluoroacetate normal Wittig olefin synthesis took place with the carbonyls of the ester groups to give vinyl ethers, e.g. (14). On the other hand, methyl chloroacetate with... 

Methyl 2-butenoate 3-Methyl- 1-butyne 2-Methylbutyl acetate Methyl chloroacetate Methyl cyanoacetate Methyl cyclobutanecarboxylate Methylcyclohexane 6.75... 

The reaction of saccharin with sodium hydroxide results in substitution of the imide hydrogen atom of saccharin with sodium, giving a sodium salt (3.2.75). The resulting product is reacted with methyl chloroacetate, giving the saccharin-substituted acetic acid methyl ester (3.2.76). Upon reaction with sodium methoxide in dimethylsuhoxide, the product undergoes... 

Synthesis The reaction of benzothiazolo-3(2H)-one-1,1-dioxide with methyl chloroacetate gives the methyl 2(3H) acetate derivative, which is isomerized with sodium methoxide in toluene/terf-butanol yielding methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1 -dioxide. The subsequent methylation with methyl iodide in methanol yields the 2-methyl compound. Finally this compound is treated with 2-amino-5-methylthiazole in xylene (Trummlitz et al. (Thomae GmbH), 1979 Trummlitz et al., 1989 Kleemann et al., 1999). 

Lehn synthesised guanidinium-based cationic steroids incorporating an acylhy-drazone linker using the approach shown in Fig. 9 [141]. The synthesis was developed from a polyamine scaffold by guanidination of the primary amino groups and alkylation of the secondary amine with methyl chloroacetate to introduce the ester moiety required to form a hydrazide group by reaction with hydrazine monohydrate. Cationic steroid hydrazones were then prepared via an acetic acid catalysed reaction with cholestanones, which demonstrated high transfection efficiency and low toxicity in a variety of cell lines [141]. 

The reaction of 2-oxo-4-thioxopyrimidin-5-carbonitrile 117 with methyl chloroacetate in the presence of methanolic sodium ethoxide gave thieno[2,3-d]pyrimidine 118 [84JCS(P1)2447]. 2,4-Dithioxopyrimidine-5-carbonitrile 119 was reacted with acetonitrile or various a-chlorocarbonyl compounds in ethanol containing sodium acetate to give the corresponding thieno[2,3-d]pyrimidines 120 (91PS223). 

R,2S,5R)-5-Methyl-2-(1-raethyl-1-phenylethyl)cyclohexyl chloroacetate Acetic acid, chloro-, 5-methyl-2-(l-methyl-l-phenylethyl)cyclohexyl ester, [lR-(la,2B,5a)]- (10) (71804-27-8)... 

Methyl chloroacetate is indexed at acetic acid, chloro-, methyl ester. 

With the V0(0 ter-C Hj)j—Al2(C2Hj)3Clj catalytic system and with ethyl tri-chloroacetate acting as a promoter , polyethylene with very narrow MWD was obtained (Q = 2.1 to 2.6 values from fractionation data). Similar behaviour was observed for a modified Carrick-like catalytic system prepared from a soluble vanadium compound, Sn(CgH5)4 and AlBrj, in the presence of methyl trichloro-acetate as promoter . 

The addition of a six-membered ring between C-14 and Na in tetrahydro-alstonine (120) was achieved by oxidation with mercuric acetate, which gave the unstable 3,14-enamine (121) via the corresponding C-3, Nb-immonium salt. The reaction of (121) with methyl chloroacetate resulted in alkylation at C-14 and cyclisation, with formation of the crystalline hexacyclic enamine (122), reduction of which afforded the 3,14-dihydro-derivative (123) (Scheme 12). 

The reaction of 3-nitropyridme with methyl chloroacetate under basic conditions provides ethyl nitropyridyl acetates, followed by their catalytic hydrogenation and cyclization into azaoxindoles (Scheme 78) [59, 60, 197]. 

Isoamyl chloroacetate 1,3-Butanediol methyl ether acetate Styrene Phenyl acetate Ethylbenzene m-Xylene o-Xylene p-Xylene... 

Isopropyl acetate Methyl acetate Methyl chloroacetate l-Methoxy-2-propyl acetate Methyl glycol acetate 5-Norbornen-2-yl acetate w-Pentyl acetate w-Propyl acetate Vinyl acetate... 

Ethereal butyllithium added dropwise under Ng to a stirred ethereal soln. of 3-thiophenealdehyde ethylene acetal, refluxed 20 min., ice-cooled, sulfur added in small portions, refluxed 1 hr., cooled to room temp., methyl chloroacetate in ether added dropwise, allowed to stand overnight, poured into ice-cold 2 N HGl, the dry ether extract added dropwise to a soln. of Na in ethanol, and refluxed 5 hrs. 2-thieno[2,3-b]thiophenecarboxylic acid. Y 94%. S. Grono-... 

Dichloroacetic acid is produced in the laboratory by the reaction of chloral hydrate [302-17-0] with sodium cyanide (31). It has been manufactured by the chlorination of acetic and chloroacetic acids (32), reduction of trichloroacetic acid (33), hydrolysis of pentachloroethane [76-01-7] (34), and hydrolysis of dichloroacetyl chloride. Due to similar boiling points, the separation of dichloroacetic acid from chloroacetic acid is not practical by conventional distillation. However, this separation has been accompHshed by the addition of a eotropeforming hydrocarbons such as bromoben2ene (35) or by distillation of the methyl or ethyl ester. 

Similarly, 3-(5-mercapto-l,2,4-triazol-3-yl)-7-methyl-l,4-dihydro-4-oxo-l,8-naphthyridines 432, after reaction with substituted benzaldehydes, chloroacetic acid in the presence of the mixture of acetic anhydride and acetic acid, gives the corresponding 3-(6-arylidene-5-oxo-5,6-dihydro-thiazolo[3,2- ]-l,2,4-triazol-2-yl)-7-methyl-l,4-dihydro4-oxo-1,8-naphthyridines 433 (Equation 92) <2002EJC323>. 

Analogously, 5-(pyrimidylsulfanyl)methyl-l,2,4-triazolidine-3-thione 436 reacts with chloroacetic acid, sodium acetate in acetic acid, to give 188 in 77% yield (Equation 94) <2003PS(178)2431>. 

Uses Manufacture of acetate rayon, acetic anhydride, acetone, acetyl compounds, cellulose acetates, chloroacetic acid, ethyl alcohol, ketene, methyl ethyl ketone, vinyl acetate, plastics and rubbers in tanning laundry sour acidulate and preservative in foods printing calico and dyeing silk solvent for gums, resins, volatile oils and other substances manufacture of nylon and fiber, vitamins, antibiotics and hormones production of insecticides, dyes, photographic chemicals, stain removers latex coagulant textile printing. 

In a closely related investigation, designed to generate vinyl alcohol in solution, divinyl hemiorthoformate [68] was detected as an intermediate in the hydrolyses of divinyloxymethyl dichloro- and trichloro-acetate [67] (Capon et al., 1981b). It is interesting that methyl vinyl hemiorthoformate could not be detected in the hydrolysis of methoxyvinyloxymethyl acetate and chloroacetate under similar conditions. So dimethyl and divinyl hemiorthoformate appear to be more stable than methyl vinyl hemiorthoformate. 

Methyl-2-(l-methyl-1-phenylethyl)cyclohexanone, (2S.5R)- Cyclohexanone, 5-methyl-2-(l-methyl-l-phenylethyl-, (2S-cis)- (65337-06-6), 65, 203 5-Methyl-2-(l-methyl-l-phenylethyl)cyclohexyl chloroacetate, (1R,2S,5R)- Acetic acid, chloro-, 5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester, [lR-(la,Z0,5a)]- (71804-27-8), 65, 203 5-Methyl-2-[l-methyl-l-(phenylmethylthio)ethyl]cyclohexanone, cis- and trans 65, 215... 

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