Hydrochloric Acid → cis-3,5-Dimethylcyclohexane-1-carboxylic acid

Temperature

80 °C

2-((3S,5R)-3,5-Dimethyl-cyclohexylidene)-[1,3]dithiane (8.36 g, 0.036 mmol) and TFA (9.5 mL, 0.12 mol) were placed in acetonitrile (480 mL) and water (120 mL) and the mixture was heated at 65° C. for 1 h. 30% Aqueous hydrogen peroxide (48 mL, 0.49 mol) was added carefully and the mixture was warmed to 80° C. slowly. After 1 h, the reaction mixture was cooled to 40° C. and was added slowly to an aqueous solution of NaOH (6N, 475 mL). The resulting mixture was cooled to 0° C. and acidified with aqueous 6N HCl. The acetonitrile was removed by rotary evaporation. The residue was extracted with dichloromethane (100 mL×5) was dried (MgSO4) and was evaporated in vacuo to yield the title compound as a white wax (4.1 g, 72%). MH+157.

1. temperaturethe reaction mixture was cooled to 40° C.
2. temperatureThe resulting mixture was cooled to 0° C.
3. customThe acetonitrile was removed by rotary evaporation
4. extractionThe residue was extracted with dichloromethane (100 mL×5)
5. dry with materialwas dried (MgSO4)
6. customwas evaporated in vacuo

ORD record

ord-4fdd8f6388ac42c6aab3776346f75e86

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07332485B2