Carbon Dioxide → 4-(Butylthio)benzoic acid

Reaction equation

C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([S:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:9][CH:8]=1.[C:18](=[O:20])=[O:19]>C1COCC1>[CH2:14]([S:13][C:10]1[CH:11]=[CH:12][C:7]([C:18]([OH:20])=[O:19])=[CH:8][CH:9]=1)[CH2:15][CH2:16][CH3:17]

Participants

Procedure

n-Butyllithium (6.8 ml, 10.0M in hexane, 0.068 mol) was added to a stirred, cooled (-78° C.) solution of compound 1 (16.56 g, 0.067 mol) in dry THF (200 ml), under dry nitrogen at -78° C. The mixture was maintained under these conditions for a further 0.5 h (glc analysis confirmed a complete reaction) before being poured into a slurry of `Cardice` and dry THF. The mixture was allowed to warm to room temperature overnight. The combined organic extracts were evaporated in vacuo and the residue was dissolved in boiling acetic acid. Ice (400 g) was added to the solution and the product was filtered off and dried in vacuo (KOH, P2O5).