Methyl Acrylate → Propanoic acid, 3-((2-methoxy-2-oxoethyl)thio)-, methyl ester

HRID 902504Notes

Reaction equation

HRID 902504 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].[C:7]([O:11][CH3:12])(=[O:10])[CH2:8][SH:9].N1CCCCC1>>[CH3:6][O:5][C:1](=[O:4])[CH2:2][CH2:3][S:9][CH2:8][C:7]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 3

HCID 7294Methyl AcrylateHCID 8082PiperidineHCID 16907Methyl Thioglycolate

Product 1

HCID 81891Propanoic acid, 3-((2-methoxy-2-oxoethyl)thio)-, methyl esterYield 99.9%

Conditions

Temperature
50 °C

Procedure

Methyl acrylate (99.16 mL, 1.1 mol) was added slowly to a solution of methyl thioglycolate (91 mL, 1 mol) and piperidine (2 mL) while maintaining the temperature of reaction mixture at 50° C. The reaction mixture was stirred at 50° C. for 2 h. Excess methyl acrylate and piperidine were distilled off under high vacuum to yield 192 g (99%) of 3-methoxycarbonylmethylsulfanyl-propionic acid methyl ester as a colorless viscous oil. 1H NMR (400 MHz, CDCl3) δ 2.63 (d, J=7.2 Hz, 2H), 2.89 (d, J=7.2 Hz, 2H), 3.24 (s, 2H), 3.68 (s, 3H), 3.72 (s, 3H) ppm.

Workup

  1. temperaturewhile maintaining
  2. customthe temperature of reaction mixture at 50° C
  3. distillationExcess methyl acrylate and piperidine were distilled off under high vacuum

Sources & evidence

ORD record
ord-66fa8b2735a34493a54cfd448e423691
Source dataset
uspto-grants-2008_04
Patent number
US07365200B2

Reaction notes

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