Benzyl 4-Hydroxybenzoate → Benzyl 4-(methoxycarbonylmethoxy)benzoate

Reaction equation

[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1.Br[CH2:19][C:20]([O:22][CH3:23])=[O:21].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:23][O:22][C:20]([CH2:19][O:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1)=[O:21]

Participants

Procedure

A mixture of benzyl 4-hydroxybenzoate (169.0g.), methyl bromoacetate (122.4g.) and anhydrous potassium carbonate (200g.) in acetone (500ml.) (analytical grade) was stirred and heated under reflux for 16 hours. The mixture was then filtered and the filtrate evaporated in vacuo. The semi-solid residue obtained was separated by filtration. The solid thus obtained was washed with cold (0°-5° C.) petroleum ether (b.p. 60°-80° C.) (50ml.) to give benzyl 4-(methoxycarbonylmethoxy)benzoate, m.p. 63°-66° C.