Methyl Ethyl Ketone → 6-Benzyloxynaphthalene-2-carboxylic acid methyl ester

Participants

Reaction Steps

Methyl 6-hydroxy-2-naphthoate (50 g), benzyl chloride (31.3 g), anhydrous potassium carbonate (100 g) and 2-butanone (350 ml) were stirred and refluxed together for 17 hours. Tlc showed the presence of some unreacted starting material and so a further 5 g benzyl chloride was added and refluxing continued for 3 hours. The product was isolated by pouring into water (1 liter), extracting the aqueous layer with 3×600 ml and 2×350 ml 2-butanone, followed by evaporation to dryness. The residue (65.7 g brown solid) was chromatographed over alumina (330 g) and silica gel (130 g) in dichloromethane, and the product was recrystallised from ethyl acetate (350 ml). Yield 37.3 g (51.6% theory) mpt 148.4°-149.3° C.

Provenance & Evidence