Water → (4-Methoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methanol

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Reaction Steps

A solution of 5-methoxybenzocyclobutene-1-carboxylic acid (32.0 g) in ether (1.2 1) is added dropwise to a stirred suspension of LAH (15.5 g) in ether (650 ml) under nitrogen. The reaction mixture is stirred at RT for 4 hours, after which, water (15.5 ml), 15% NaOH (15.5 ml) and a second portion of water added (46 ml) sequentially to the reaction mixture resulting in the formation of a precipitate. The ethereal layer is filtered, dried over Na2SO4, filtered and concentrated in vacuo yielding the desired product as an oil.

Provenance & Evidence