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 (479) of the aldehyde as a clear oil, 1H NMR (300 MHz, CDCl3): 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-5c338d92bb044ace93a01ba19e99d1a5

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05874449