Dimethyl Sulfoxide → 2-[(3,4-Dimethylphenyl)oxy]acetaldehyde

Temperature

-78 °C

A cooled (−78° C.) solution of oxalyl chloride (0.76 ml; 9.000 mmol) in anhydrous DCM (40 ml) was treated dropwise with a solution of dimethyl sulfoxide (1.40 ml; 18.000 mmol) in anhydrous DCM (6 ml). After 10 min., a solution of 2-(3,4-dimethyl-phenoxy)-ethanol (0.997 g; 6.000 mmol) in DCM (12 ml) was added dropwise, and the reaction mixture was further stirred at −78° C. for 30 min. TEA (4.17 ml; 30.000 mmol) was then added dropwise, and after 10 min. the resulting mixture was allowed to warm-up to 0° C. before a mixture of water (4 ml) and DCM (40 ml) was added. The aq. layer was extracted with DCM (2×40 ml), and the mixed organic layers were then washed with aq. sat. NaHCO3 (30 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure to give (3,4-dimethyl-phenoxy)-acetaldehyde as a yellow oil (0.985 g; 99%).

1. waitafter 10 min. the resulting mixture was allowed
2. additionwas added
3. extractionThe aq. layer was extracted with DCM (2×40 ml)
4. washthe mixed organic layers were then washed with aq. sat. NaHCO3 (30 ml)
5. dry with materialdried over anh. MgSO4
6. filtrationfiltered
7. concentrationconcentrated to dryness under reduced pressure

ORD record

ord-92efd8ea2ddb48b09b6fbf5ef57dc103

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188082B2