Hydrochloric Acid → 3-(Benzyloxy)benzoic acid

Participants

Reaction Steps

A solution of methyl 3-benzyloxybenzoate (38.0 g) and 5 N NaOH solution (207 ml) in 1,2-dimethoxyethane (207 ml) was stirred at room temperature for 3 hours 30 minutes and at 100° C. for 1 hour 20 minutes. The reaction mixture was cooled with ice water, mixed with 6N HCl (1.1 mole), and extracted with diethyl ether. The extract was washed with brine, dried over MgSO4, and evaporated in vacuo to afford 3-benzyloxybenzoic acid (34.96 g) as a colorless powder. (-) APCI-MS (m/z): 227 (M+ -1) mp: 134.1-135.8° C. IR (Nujol): 2700-2150, 1680, 1250 cm-1NMR (CDCl3, δ): 5.12 (2H, s), 7.19-7.49 (7H, m), 7.71-7.76 (2H, m)

Provenance & Evidence