Tetrahydrofuran → Methyl 2-(5-chloro-2-hydroxyphenyl)acetate

Participants

Reaction Steps

A mixture of methyl methylthiomethyl sulfoxide (11.7 g), 40% solution of benzyltrimethylammonium hydroxide in methanol (7.5 mL), 5-chloro-2-methoxymethoxybenzaldehyde (9.43 g) and tetrahydrofuran (150 mL) was heated under reflux for 20 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. A mixture of the obtained residue and 10% hydrogen chloride-methanol (100 mL) was heated under reflux for 15 hrs. The reaction mixture was concentrated, and ethyl acetate was added to the residue. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (7.24 g, 91%) of methyl 2-(5-chloro-2-hydroxyphenyl)acetate from a fraction eluted with ethyl acetate-hexane (1:4, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 84-85° C.

Provenance & Evidence