2,4-Dihydroxybenzaldehyde → 2-Hydroxy-4-(methoxymethoxy)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

Oven-dried potassium carbonate (1.38 g, 10 mmol) was added to an ice cooled solution of 2,4-dihydroxy-benzaldehyde (1.38 g, 10 mmol) in 10 mL of acetone. MOMCl (1.54 mL, 20 mmol) was added drop-wise and the mixture was stirred at 0° C. for one hour, after which it was gradually allowed to come to RT. The reaction was further stirred for 24 hours at RT and then poured into ice water with vigorous stirring. A Buff colored solid precipitated. The solid was filtered, dried and recrystallized from MeOH:DCM (ca. 30:5 mL) to obtain 1.31 g (72%) of white solid: mp 52-53° C. [Lit.(65) 50-51° C.]; TLC Rf0.43 in hexanes:EtOAc (2:1), 1H NMR (400 MHz, CDCl3) δ 11.38 (s, 1H, OH), 9.74 (s, 1H, CHO), 7.46-7.44 (d, 1H, J=8.4 Hz, Ar—H6), 6.66-6.64 (dd, 1H, 2J=8.4 Hz, 3J=2 Hz, Ar—H5), 6.60 (d, 1H, 3J=2 Hz), 5.24 (s, 2H, O—CH2—O), 3.48 (s, 3H, OCH3). 13C NMR (100 MHz, CDCl3) δ 194.8, 164.5, 164.4, 135.6, 116.2, 109.3, 103.6, 94.3, 56.7.

Provenance & Evidence