Dimethyl Sulfoxide → 3-(4-Chlorophenyl)propanal

To a stirred solution of oxalyl chloride (2.04 ml) in dichloromethane (40 ml) at −78° C. was added dimethyl sulphoxide (3.33 ml), and the reaction stirred for 10 min. 3-(4-Chlorophenyl)propanol (2.0 g) in dichloromethane (20 ml) was added and the reaction stirred at −78° C. for 75 min. Triethylamine (11.53 ml) was added, the reaction allowed to warm to room temperature, and stirred for 30 min. Water (150 ml) was added, and the reaction extracted with dichloromethane (2×100 ml). The combined organic extracts were washed with water (3×100 ml), dried over magnesium sulphate (2 g), and the solvent removed in vacuo to yield a yellow oil. This was purified by flash chromatography (silica, eluent dichloromethane) to yield the title compound as a pale yellow oil (0.96 g).

1. stirringthe reaction stirred at −78° C. for 75 min
2. stirringstirred for 30 min
3. extractionthe reaction extracted with dichloromethane (2×100 ml)
4. washThe combined organic extracts were washed with water (3×100 ml)
5. dry with materialdried over magnesium sulphate (2 g)
6. customthe solvent removed in vacuo
7. customto yield a yellow oil
8. customThis was purified by flash chromatography (silica, eluent dichloromethane)

ORD record

ord-388446210e0c47deb6ffb08b53ee68f6

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06462042B1