Methyl Acrylate → Methyl 3-(laurylthio)propionate

HRID 1460133Notes

Reaction equation

HRID 1460133 reaction equation
[CH2:1]([SH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:14]([O:18][CH3:19])(=[O:17])[CH:15]=[CH2:16]>O[Li].O>[CH2:1]([S:13][CH2:16][CH2:15][C:14]([O:18][CH3:19])=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 81951-Dodecanethiol

Product 1

HCID 88227Methyl 3-(laurylthio)propionateYield 100.8%

Reagents, catalysts & solvents 1

HCID 168937Lithium hydroxide, monohydrateCatalyst

Procedure

Into the same type of equipment used in Example 1 was charged 405 grams of 98% 1-dodecanethiol with stirring to 1.0 grams of LiOH·H2O and 181 grams of 99% methyl acrylate. The addition was over a period of 20 minutes and the temperature increased to 80°-85° C. The reaction was stirred an extra 2 hours at 85°-95° C. The reaction mixture was then stripped at 122° C. and 10 mm pressure. 582 grams of product was obtained. Product analysis by GC indicated a purity of 92.1%.

Workup

  1. additionThe addition
  2. temperaturethe temperature increased to 80°-85° C
  3. customwas then stripped at 122° C.

Sources & evidence

ORD record
ord-39f9ead76780429e96fc0fee28bcbe2b
Source dataset
uspto-grants-1991_12
Patent number
US05069819

Reaction notes

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