Methanol → Methyl 4-benzyloxy-2-ethyl-3-methylbenzoate
Reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[C:11]([CH2:18][CH3:19])[C:10]=1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH3:26]O>>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([O:15][CH3:26])=[O:14])=[C:11]([CH2:18][CH3:19])[C:10]=1[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
4
Conditions
- Temperature
- 67 °C
Procedure
19.7 g of 4-benzyloxy-2-ethyl-3-methylbenzoic acid (D1) are dissolved in 200 ml of methanol. 5.0 ml of H2SO4 (95-98%, extra pure) are subsequently added. The reaction solution is heated under reflux at 67° C. for 18 h overnight and subsequently evaporated to ⅓ of the volume in vacuo, and 200 ml of water are added. The mixture is then extracted twice with 200 ml of ethyl acetate each time. The combined organic phases are subsequently washed with saturated NaHCO3 solution, dried over Na2SO4 and evaporated in vacuo, giving 17.5 g of the title compound as a colourless oil; MS: 285.2 (MH+); TLC: Rf=0.72 (cyclohexane/methyl tert-butyl ether 1:1 parts by volume).