Acetic Acid → 4-Bromo-2,6-bis(hydroxymethyl)phenol

Participants

Reaction Steps

In a 2 liter graduated bottle equipped with magnetic stirrer was suspended 101 g (585 mmol)4-bromophenol in 500 ml water. A solution comprised of 28.9 g (723 mmol) NaOH in 100 ml water was added all at once to the reaction mixture. 128 g (1.58 mol) of formaldehyde solution (Aldrich, 37% in water) was then added and the reaction mixture was covered in aluminum foil and allowed to sit for 45 days at ambient temperature. Glacial acetic acid (60 ml, 1.0 mol) was added to precipitate out the solid. The solid was washed with ample amounts of water and then dried under high vacuum (0.1 mm Hg) for 20 hours at 50° C. and ambient temperature for 48 hours to give 101.2 g (74%) of a light orange solid. 1H NMR (DMF-d7) delta: 8.21 (s, 1H, phenol OH), 7.56 (s, 2H, Ar—H), 5.70 (s, 2H, OH), 4.90 (s, 4H, CH2).

Provenance & Evidence