Water → 3-(Benzyloxy)propanal

Participants

Reaction Steps

To a solution of 15.6 mL of oxalyl chloride in 420 mL of dichloromethane at −78° C. was added 24.0 mL of dimethyl sufoxide and stirred for 10 min, followed by addition of 19.95 g (0.12 mol) of 3-benzyloxy-1-propanol and stirred for 45 min. After adding 58.5 mL of triethylamine, the mixture was stirred in an ice bath for 20 min. 42 mL of water was added and the mixture was extracted with 660 mL of benzene/diethyl ether (1/1). The organic layer was washed with 5% hydrochloric acid (42 mL), water (42 mL) and brine (42 mL), dried over anhydrous sodium sulfate and concentrated. Distillation at 68-70° C./3 mmHg gave 17.0 g of a liquid in 86.3% yield. 1H NMR (CDCl3): δ 9.79 (t, J=1.8 Hz, 1H, CHO), 7.35-7.31 (m, 5H, ArH), 4.53 (s, 2H, ArCH2O), 3.81 (t, J=6.0 Hz, 2H, CH2O), 2.69 (td, J=6.0, 1.8 Hz, 2H, CH2C═O). 13C NMR (CDCl3): δ 201.08, 137.72, 128.35, 127.69, 127.62, 73.18, 63.75, 43.81. EIMS m/z 164 (M+), 107, 91, 79.

Provenance & Evidence