4-Hydroxybenzoic Acid → Benzoic acid, 4-hydroxy-, 2-methylbutyl ester

Reaction equation

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

Participants

Procedure

4.0 g of p-hydroxybenzoic acid and 12.5 g of (-)-2-methylbutanol were refluxed for 6 hours in toluene in the presence of sulfuric acid, while removing the generated water out from the reaction system. Subsequently, the reaction solution was washed with water to remove sulfuric acid out. The reaction solution was then dried and concentrated, and the concentrate was purified by column chromatography, to obtain 5.0 g of the objective ester compound (liquid state at room temperature, [α]D23 =4.9° (CHCl3)). (Yield: 83%)