1-Octanethiol → 3,4,4-trifluoro-3-butenethioic acid, S-octyl ester

HRID 54735

Reaction equation

HRID 54735 reaction equation
[F:1][C:2](=[C:7]([F:9])[F:8])[CH2:3][C:4](Cl)=[O:5].[CH2:10]([SH:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>>[F:1][C:2](=[C:7]([F:9])[F:8])[CH2:3][C:4](=[O:5])[S:18][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

3

Reactant 2

HCID 81441-OctanethiolHCID 109207893,4,4-Trifluoro-3-butenoyl chloride

Product 1

HCID 152391923,4,4-trifluoro-3-butenethioic acid, S-octyl esterYield 91.3%

Conditions

Temperature
70 °C

Procedure

A mixture of 3,4,4-trifluoro-3-butenoyl chloride (1.7 g, 0.0107 mole) and 1-octanethiol (0.72 g, 0.0049 mole) is heated at 70° C. for 12 h. The crude product is purified by passing through a short column of silica gel to give 1.2 g of the desired product as a pale yellow oil, a 91% yield.

Workup

  1. customThe crude product is purified

Sources & evidence

ORD record
ord-eb0dbc9d20ca481b847892b364cfb881
Source dataset
uspto-grants-1997_04
Patent number
US05623084

Linked notes

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