Acetone → Benzoic acid, 2-ethoxy-4-methyl-, ethyl ester

反応式

[OH:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:18](I)[CH3:19].[CH3:21][C:22](C)=O>>[CH2:21]([O:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:18][CH3:19])=[O:5])[CH3:22]

参加物

反応物 4

HCID 180Acetone

HCID 57882-Hydroxy-p-toluic acid

HCID 6340Iodoethane

HCID 11430Potassium Carbonate

生成物 1

HCID 11816602Benzoic acid, 2-ethoxy-4-methyl-, ethyl ester収率 85%

実験手順

To a mixture of 2-hydroxy-4-methylbenzoic acid (5.0 g, 32.9 mmol), K2CO3 (18.9 g, 136.6 mmol) and acetone (50 mL) was added ethyl iodide (41.0 g, 263.2 mmol). The mixture was stirred at room temperature for 3 days. After filtration, the organic layer was concentrated to afford ethyl 2-ethoxy-4-methylbenzoate as colorless oil (5.7 g, 85%), which was used directly for next step.