1-Butanol → n-Butyl 3-hydroxy-1-adamantanecarboxylate

反応式

[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][C:4]([C:12]([OH:14])=[O:13])([CH2:5]3)[CH2:3]1)[CH2:9]2.[CH2:15](O)[CH2:16][CH2:17][CH3:18].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][C:4]([C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:13])([CH2:5]3)[CH2:3]1)[CH2:9]2

参加物

実験手順

To 900 ml of toluene were added 300 mmol of the obtained 3-hydroxy-1-adamantanecarboxylic acid, 450 mmol of n-butanol, and 15 mmol of sulfuric acid, and the resultant mixture was stirred under reflux of toluene for 5 hours. The reaction mixture was concentrated and then subjected to column chromatography on a silica gel to give n-butyl 3-hydroxy-1-adamantanecarboxylate (yield: 94.1%). The conversion rate from 3-hydroxy-1-adamantanecarboxylic acid was 99%.