Dimethyl Sulfoxide → Benzenepropanal

Oxalyl chloride (2.90 g; 2.29 mmol) in methylene chloride (50 ml), cooled to −78° C., was treated with dimethylsulfoxide (3.4 ml) in 10 ml of methylene chloride. After stirring for 5 min, 3-phenyl-1-propanol (2.72 g; 20 mmol) in 20 ml of methylene chloride was added, and the resulting mixture was stirred at −78° C. for 15 min, treated with 14 ml of triethylamine, stirred an additional 15 min, and poured into 100 ml of water. The layers were separated, the organic phase was dried and concentrated, and the crude residue was purified on a silica gel column, eluting with 10% ethyl acetate in hexane, to obtain 1.27 g (47%) of the aldehyde as a clear oil. 1H NMR (300 MHz, CDC3): δ 2.80 (m, 2H); 2.98 (m, 2H); 7.27 (m, 5H); 9.81 (2, 1H).

1. stirringthe resulting mixture was stirred at −78° C. for 15 min
2. stirringstirred an additional 15 min
3. customThe layers were separated
4. customthe organic phase was dried
5. concentrationconcentrated
6. customthe crude residue was purified on a silica gel column
7. washeluting with 10% ethyl acetate in hexane

ORD record

ord-e70f6f0b0b8f44c7aa5e6c5f3a64b776

Source dataset

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06943187B2