Dimethyl Sulfide → HCID 60026511, compound

To a chilled (−78° C.) solution of (1-methoxymethyl-1-methylbut-3-enyl)benzene (1.67 g, 8.77 mmol) in methanol-dichloromethane was bubbled ozone gas until the solution turned blue. The excess ozone was then purged from the mixture with oxygen and then dimethyl sulfide (5 mL, 68 mmol) was added and the mixture was warmed to room temperature and stirred overnight. The mixture was then concentrated in vacuo to remove the excess dimethyl sulfide and diluted with 20 mL of ammonium chloride and extracted with three 15 mL portions of ethyl acetate. The combined organic layers were washed with three 15 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford an oil which corresponded to the dimethyl acetal by 1H-NMR. The crude product was diluted with 40 mL of acetone and p-TsOH (300 mg, 1.57 mmol) was added and the mixture was stirred at room temperature for 2 hours. The reaction was monitored by 1H-NMR and indicated the presence of aldehyde and dimethyl acetal. The reaction was refluxed for 4 hours and monitored by TLC (ethyl acetate-hexanes (1:9)) and then cooled and diluted with saturated aqueous sodium bicarbonate solution and extracted with three 15 mL portions of ethyl acetate. The combined organic layers were washed with two 10 mL portions of saturated aqueous sodium bicarbonate solution, two 10 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 1.45 g (85.9% yield) of 4-methoxy-3-methyl-3-phenylbutyraldehyde.

1. customwas bubbled ozone gas until the solution
2. customThe excess ozone was then purged from the mixture with oxygen
3. concentrationThe mixture was then concentrated in vacuo
4. customto remove the excess dimethyl sulfide
5. additiondiluted with 20 mL of ammonium chloride
6. extractionextracted with three 15 mL portions of ethyl acetate
7. washThe combined organic layers were washed with three 15 mL portions of brine
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customto afford an oil which
12. additionwas added
13. stirringthe mixture was stirred at room temperature for 2 hours
14. temperatureThe reaction was refluxed for 4 hours
15. temperaturecooled
16. extractionextracted with three 15 mL portions of ethyl acetate
17. washThe combined organic layers were washed with two 10 mL portions of saturated aqueous sodium bicarbonate solution, two 10 mL portions of brine
18. dry with materialdried over magnesium sulfate
19. filtrationfiltered
20. concentrationconcentrated in vacuo

ORD record

ord-fbbf44d406fc450dba3e4ccf01eec373

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08741897B2