ChemicalBook CAS DataBase List METHYL ALPHA-CHLOROACRYLATE

METHYL ALPHA-CHLOROACRYLATE synthesis

4synthesis methods

Product Name:METHYL ALPHA-CHLOROACRYLATE
CAS Number:80-63-7
Molecular formula:C4H5ClO2
Molecular Weight:120.53

50-00-0 Synthesis

50-00-0
841 suppliers
$10.00/25g

96-34-4 Synthesis

96-34-4
337 suppliers
$10.00/25g

80-63-7
125 suppliers
$85.00/5g

Yield:80-63-7 58.1%

Reaction Conditions:

Stage #1:methyl chloroacetate with Dimethyl oxalate;sodium methylate in dimethyl sulfoxide at 15 - 25; for 1 h;Inert atmosphere;
Stage #2:formaldehyd with 2,6-di-tert-butyl-4-methyl-phenol in dimethyl sulfoxide at 20 - 25; for 1 h;Inert atmosphere;

Steps:

9.a; 9.b synthesis 2-chloroacrylic acid methyl ester
To the 3000 mL reaction flask was added 217 g (2.0 mol) of methyl chloroacetate, 256.0 g (2.16 mol) of dimethyl oxalate and 1104.0 g (14. lmol) of dimethylsulfoxide, and the mixture was replaced with nitrogen twice, (2.3 mol) of sodium methoxide solid was added in portions, and the temperature was controlled at 15 to 25 degrees Celsius. After 1 hour, the reaction mixture was charged and the reaction solution was concentrated under reduced pressure, and the degree of vacuum was equal to or higher than 0.95 MPa , The reaction temperature of 25 degrees Celsius, concentrated two hours, the sampling control, methanol content of 9.4%, methyl fluoride content of 0.3%, the reaction qualified, adding acetic acid quenching reaction solution, adding polymerization inhibitor 2,6-Tert-butyl p-cresol 0.1g, and then added in batches of paraformaldehyde 60g (2.0mol), the control temperature of 20 ~ 25 degrees Celsius, after the completion of heating, stirring 1 hour, sampling control, enol sodium salt intermediate 0.15 %, 2% methyl methacrylate content of 9.0%, crude yield of 84.0%. b, Purification : After the crude reaction solution obtained above, and water was added 184.0 g (10.2 mol), stir at room temperature after the start distillation under reduced pressure, the reaction solution was slowly warmed to control the degree of vacuum 0.098 MPa, total reflux started, until the vapor temperature was stabilized, start the crude product was detected receiving phase temperature of 25 to 40 ° C fractions, the receiving tank with coolant to cool the back reception using two recovery tank, the reaction solution was slowly warmed to a temperature of 75 ° C, stop receiving collected 250.0g of crude product received content of 63% (GC), the crude product was washed with a saturated aqueous sodium chloride was added 250.0g once, the organic layer was layered to give 150g, continue after washed twice, to give 145g product, of anhydrous sodium sulfate was added 20g, and dried to give 140 g of product, total yield 58.1%, GC purity 99.3%.

References:

Waterstone PharmaceuticalsHubeiCo., Ltd.;Wang, Nian;Huang, Kun;Yang, QiongFeng;Song, Wei CN104478715, 2016, B Location in patent:Paragraph 0106; 0107; 0108; 0109; 0110; 0111; 0112

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