Dimethyl Sulfoxide → α,α,3-Trimethylbenzeneacetaldehyde

To a solution of oxalyl chloride (15.1 g, 119 mmol) in tetrahydrofuran (150 ml) was dropwise added a solution of dimethyl-sulfoxide (16.8 ml, 237 mmol) in tetrahydrofuran (50 ml) at −78° C., and the mixture was stirred for 5 min. A solution of 2-methyl-2-(3-methylphenyl)propan-1-ol (12.99 g, 79.09 mmol) in tetrahydrofuran (80 ml) was added at −78° C., and the mixture was stirred for 15 min. Triethylamine (66.1 ml, 475 mmol) was added thereto, and the mixture was warmed to room temperature. The reaction mixture was poured into water and extracted twice with ethyl acetate. The recovered organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1) to give the objective substance.

1. stirringthe mixture was stirred for 15 min
2. extractionextracted twice with ethyl acetate
3. dry with materialThe recovered organic layer was dried over anhydrous magnesium sulfate
4. customthe solvent was evaporated under reduced pressure
5. customThe obtained crude product
6. customwas purified by silica gel column chromatography (hexane/ethyl acetate=15/1)
7. customto give the objective substance

ORD record

ord-202c2c2500a64ed7929d044716c2195e

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06982348B2