Water → 3-(Benzyloxy)propanal

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.

1. stirringstirred for 45 min
2. stirringthe mixture was stirred in an ice bath for 20 min
3. extractionthe mixture was extracted with 660 mL of benzene/diethyl ether (1/1)
4. washThe organic layer was washed with 5% hydrochloric acid (42 mL), water (42 mL) and brine (42 mL)
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated
7. distillationDistillation at 68-70° C./3 mmHg

ORD record

ord-ca9b0dccb13e46f188ffadcb3ade692a

Source dataset

uspto-grants-2002_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06335364B1