Water → 3,4,5-Tris(benzyloxy)benzoic Acid

Participants

Reaction Steps

To a mixture of methyl 3,4,5-tribenzyloxybenzoate (15) (20.60 g, 45.30 mmol) in 2-propanol (200 mL) was added a solution of potassium hydroxide (3.50 g, 85%, 53.00 mmol) in 2-propanol (25 mL). The mixture was refluxed for 1 h, cooled, and water was added (250 mL). A white precipitate appeared, and the mixture was filtered. Recrystallisation from ethyl acetate afforded the desired compound as white crystals, m.p. 194-195° C. Yield: 17.2 g (86%). 1H NMR (300 MHz, DMSO-d6): δ=5.05 (2H, s), 5.18 (4H, s), 7.24-7.50 (17H, m), 13.4 (1H, s, broad); 13C NMR (75 MHz): δ=70.3, 74.3, 108.3, 126.1, 127.7, 128.0, 128.2, 128.3, 128.5, 136.9, 137.5, 141.0, 152.1, 167.0.

Provenance & Evidence