Methyl 3,4-methylenedioxy-5-methoxybenzoate → (7-Methoxy-1,3-benzodioxol-5-yl)methanol

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Reaction Steps

Methyl ester 5 (11.9 g, 57 mmol) in THF (50 ml) was added (slowly) dropwise to a stirred grey suspension of lithium aluminum hydride (3.4 g, 90 mmol) in THF (50 ml) at 0° C. under Ar. After stirring for 3 h at rt, the suspension was cooled to 0° C. and the reduction terminated by careful addition of Na2SO4 (sat., aq) until effervescence ceased. The precipitate was collected and the filtrant dried and concentrated in vacuo to afford benzyl alcohol 6 (9.3 g, 91%) as a colorless powder, m.p. 66–67° C. (lit. mp 66–67° C., Pettit and Singh, 1987); 1H-NMR (300 MHz):1.59 (1H, bs, —OH), 3.91 (3H, s, —OCH3) 4.59 (2H, bs, —ArCH2O—), 5.97 (2H, s, —OCH2O—), 6.56 (2H, d, J=2.1 Hz, ArH).

Provenance & Evidence