Dimethyl Sulfoxide → Phenoxyacetaldehyde

Temperature

-78 °C

At −78° C., a solution of dimethylsulphoxide (5.11 ml, 72 mmol) in DCM (50 ml) was added dropwise to a solution of oxalyl chloride (6.12 ml, 72 mmol) in DCM (150 ml). The reaction mixture was stirred for 10 min at −78° C. A solution of 2-phenoxyethanol (10.0 g, 72 mmol) in DCM (70 ml) was added dropwise. The reaction mixture was stirred at −78° C. for 10 min. A solution of triethylamine (50 ml, 360 mmol) in DCM (50 ml) was added dropwise. The reaction mixture was stirred for 10 min at −78° C. It was warmed to room temperature. The reaction mixture was washed with a 10% aqueous solution of sodium hydrogensulphate (2×200 ml) and subsequently with brine (2×200 ml). It was dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (100 g), using ethyl acetate/heptane (1:3) as eluent, to give 2.73 g of phenoxyacetaldehyde.

1. stirringThe reaction mixture was stirred at −78° C. for 10 min
2. stirringThe reaction mixture was stirred for 10 min at −78° C
3. temperatureIt was warmed to room temperature
4. washThe reaction mixture was washed with a 10% aqueous solution of sodium hydrogensulphate (2×200 ml) and subsequently with brine (2×200 ml)
5. dry with materialIt was dried over magnesium sulphate
6. customThe solvent was removed in vacuo
7. customThe crude product was purified by flash chromatography on silica (100 g)

ORD record

ord-d6d469175cb644ea9ab1c070e103756f

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06610721B2