Tetrahydrofuran → Benzyl 3-chloro-5-hydroxybenzoate

Participants

Reaction Steps

A 1.0 M solution oftetrabutylammonium fluoride in tetrahydrofuran (26.6 mL, 26.6 mmol) was added to neat benzyl ester 24 (5.00 g, 13.3 mmol), the reaction stirred 10 minutes at ambient temperature, and evaporated in vacuo. The crude product was dissolved in methylcne chloride, the solution washed with dilute aqueous NaHCO3, dried over Na2SO4, and filtered. The evaporated filtrate was then washed repeatedly with hexanes and dried in vacuo giving product 25 as a gold oil (3.40 g, 98%), 1H NMR (300 MHz, CDCl3) δ 7.35 (m, 7H), 7.1 (t, 1H, J=2.1 Hz), 5.28 (s, 2H).

Provenance & Evidence