3-Hydroxybenzaldehyde → 3-(4-Methoxyphenoxy)benzaldehyde

Participants

Reaction Steps

Triethylamine (7.1 ml, 51 mmol) was added dropwise at room temperature to a suspension of 3-hydroxybenzaldehyde (1.72 g, 14.1 mmol), 4-methoxyphenylboronic acid (3.16 g, 20.8 mmol), molecular sieves 4A powder (1.95 g) and copper (II) acetate (2.96 g, 16.3 mmol) in methylene chloride (100 ml), and the mixture was stirred for 27.5 hrs. The reaction mixture was diluted with ethyl acetate (200 ml), and the insoluble materials were filtered off and washed with ethyl acetate. The filtrate and washings were combined, washed with 10% hydrochloric acid and brine in turn and dried. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=7) to give 3-[(4-methoxy)phenoxy]benzaldehyde (596 mg, 19%) as a pale brown oil.

Provenance & Evidence