Dimethyl Sulfoxide → Benzenepropanal, alpha,alpha-dimethyl-

Temperature

-78 °C

To a solution of oxalyl chloride (10.1 g, 79.4 mmol) in methylene chloride (70 mL) at −78° C. was added dimethylsulfoxide (10.0 mL, 139 mmol). The solution was stirred at −78° C. for 10 minutes then a solution of 2,2-dimethyl-3-phenylpropanol (6.52 g, 39.7 mmol) in methylene chloride (15 mL) was added. After stirring the reaction at −78° C. for 30 minutes, triethylamine (20.1 g, 198 mmol) was added and the reaction mixture was stirred for 10 minutes, then at 0° C. for 5 minutes. The reaction mixture was quenched with saturated aqueous ammonium chloride (20 mL) and the aqueous layer was extracted with diethyl ether (2×50 mL). The organic portions were individually washed with brine (15 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was redissolved in diethyl ether and the resulting precipitate was filtered through a pad of Celite. The filtrate was concentrated under reduced pressure to provide the title compound (6.89 g) as an oil.

1. stirringAfter stirring
2. customthe reaction at −78° C. for 30 minutes
3. stirringthe reaction mixture was stirred for 10 minutes
4. waitat 0° C. for 5 minutes
5. customThe reaction mixture was quenched with saturated aqueous ammonium chloride (20 mL)
6. extractionthe aqueous layer was extracted with diethyl ether (2×50 mL)
7. washThe organic portions were individually washed with brine (15 mL)
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated under reduced pressure
10. dissolutionThe residue was redissolved in diethyl ether
11. filtrationthe resulting precipitate was filtered through a pad of Celite
12. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-b8c1230686ed4267a00e86977db70654

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06495576B2