Water → 4-(2,2-Dimethyl-1,3-dioxolan-4-yl)methoxyphenylethan-2-ol

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Reaction Steps

A solution of 27 g. (0.096 mol) of methyl 4-(2,2-dimethyl-1,3-dioxolan-4-yl)methoxyphenylacetate (3) in 200 mL of tetrahydrofuran (THF) was added slowly to a stirred suspension of 4.0 g of LAH in 300 mL of THF. The mixture was stirred 2 h at room temperature and then treated sequentially with 4 mL of water, 4 mL of 15% NaOH solution, and 12 mL of water. The mixture was filtered and the filtrate evaporated to a residue which was triturated with hexane to afford 24 g of 4-(2,2-dimethyl-1,3-dioxolan-4-yl)methoxyphenylethan-2-ol (4) as a tan solid.

Provenance & Evidence