2-Methyl-2-butene → 4-Methoxynaphthalene-1-carboxylic acid

Participants

Reaction Steps

4-Methoxy-1-naphthaldehyde (10 g, 53.72 mmol) was dissolved in t-butanol (75 ml) and 2-methyl-2-butene (35 ml) was added at room temperature. A solution of sodium chlorite (7.99 g, 70.63 mmol) and sodium dihydrogen orthophosphate (9.15 g, 76.27 mmol) in water (50 ml) was added dropwise. The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue was washed with a solution of 2MHCl (100 ml) and the solid was filtered and washed with dichloromethane (100 ml) and water (100 ml) and dried in vacuo. The solid was recrystallised from methanol to give 5.95 g (55%) of 4-methoxy-1-naphthoic acid as cream crystals.

Provenance & Evidence