Benzyl mercaptan → 2-(6-Benzylthiohexyloxy)-5-methyl-1,3-benzenedicarboxaldehyde

反応式

[O-]CC.[Na+].Br[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[C:18]([CH:19]=[O:20])=[CH:17][C:16]([CH3:21])=[CH:15][C:14]=1[CH:22]=[O:23].[CH2:24]([SH:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(O)C>[CH2:24]([S:31][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[C:18]([CH:19]=[O:20])=[CH:17][C:16]([CH3:21])=[CH:15][C:14]=1[CH:22]=[O:23])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

参加物

実験手順

A solution of sodium ethoxide (69 mg sodium, 3 mmol in ethanol 1 ml) was added to a stirred suspension of 2-(6-bromohexyloxy)-5-methyl-1,3-benzenedicarboxaldehyde (0.98 g, 3 mmol) and benzyl mercaptan (0.35 g, 3 mmol) in ethanol (10 ml) at room temperature under nitrogen. After 1 hour evaporated, water (10 ml) and 2M sodium hydroxide (2 ml) added and extracted with diethyl ether (10 ml). The extracts were washed with water, dried, filtered and evaporated to an oil (1.12 g). Chromatography on silica eluting with dichloromethane gave 2-(6-benzylthiohexyloxy)-5-methyl-1,3-benzenedicarboxaldehyde as a colourless oil.