Methyl Acrylate → Methyl 3-(octylthio)propionate

HRID 1460135Notes

Reaction equation

HRID 1460135 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][SH:9].[CH3:10][O:11][C:12](=[O:15])[CH:13]=[CH2:14]>[OH-].C([N+](C)(C)C)C1C=CC=CC=1>[CH2:8]([S:9][CH2:14][CH2:13][C:12]([O:11][CH3:10])=[O:15])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 81441-Octanethiol

Product 1

HCID 116776Methyl 3-(octylthio)propionateYield 143.6%

Reagents, catalysts & solvents 1

HCID 66854Benzyltrimethylammonium hydroxideCatalyst

Procedure

Into the same type of equipment used in Example 1, 146 grams of 1-octylthiol was added over a 40 minute period with stirring to 0.7 grams of benzyl trimethyl ammonium hydroxide and 180.6 grams of methylacrylate. Over the 1/2 hour period, the temperature of the reaction went from 25° C. to 60° C. The reaction was stirred an extra 3.0 hours wherein the temperature went from 60° C. to 28° C. The reaction mixture was stripped at 102° C. and 15 mm pressure. 333 grams of product was obtained having a purity of approximately 96.4% as measured by GC analysis.

Workup

  1. additionwas added over a 40 minute period
  2. customOver the 1/2 hour period
  3. customwent from 25° C. to 60° C
  4. customwent from 60° C. to 28° C
  5. customwas stripped at 102° C.

Sources & evidence

ORD record
ord-4fee9cec243849cb8fd2203fef11231b
Source dataset
uspto-grants-1991_12
Patent number
US05069819

Reaction notes

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