Carbon Dioxide → 2-Mercapto-3-isopropylbenzoic acid

HRID 2965

Reaction equation

HRID 2965 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[SH:10])([CH3:3])[CH3:2].CN(CCN(C)C)C.[Li]CCCC.[C:24](=[O:26])=[O:25]>C1CCCCC1>[SH:10][C:5]1[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=[CH:7][C:6]=1[C:24]([OH:26])=[O:25]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 96003Benzenethiol, 2-(1-methylethyl)-HCID 178418339Butyllithium

Product 1

HCID 106555072-Mercapto-3-isopropylbenzoic acid

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

To a solution of 1.0 mmol 2-isopropylthiophenol and 2.2 mmol TMEDA in 2 mL cyclohexane was added 2.2 mmol n-BuLi. Then after stirring 24 h it was added to solid CO2 and stirred for 16 h when extraction and chromatography provided 2-mercapto-3-isopropylbenzoic acid. The methyl ester of this was treated as in example 3 to provide the title compound.

Workup

  1. stirringstirred for 16 h
  2. extractionwhen extraction and chromatography

Sources & evidence

ORD record
ord-8bfebd9748154a9780039335f8d6e481
Source dataset
uspto-grants-1998_03
Patent number
US05731432

Linked notes

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