Hydrochloric Acid → (1S)-4-methylcyclohex-3-ene-1-carboxylic acid

Temperature

50 °C

4-Methyl-cyclohex-3-(S)-enecarboxylic acid 4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester (3.34 g, 13.2 mmol) in THF (25 mL), water (2.5 mL) and methanol (2.5 mL) was treated with lithium hydroxide monohydrate (2.8 g, 66.2 mmol) and warmed to 50° C. with stirring. After 1 h, the reaction mixture treated with 1M HCl (about 25 mL). The mixture was extracted with hexanes:ethyl acetate (200 mL:15 mL), dried over sodium sulfate, filtered and concentrated to 2.4 g of a white semi-solid. The residue was redissolved in hexanes:dichloromethane (100 mL, 95:5), washed with water, dried over sodium sulfate, filtered and concentrated to 1.68 g (91% yield) of (1S)-4-methyl-cyclohex-3-enecarboxylic acid as a white powder.

1. extractionThe mixture was extracted with hexanes
2. dry with materialethyl acetate (200 mL:15 mL), dried over sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated to 2.4 g of a white semi-solid
5. dissolutionThe residue was redissolved in hexanes
6. washdichloromethane (100 mL, 95:5), washed with water
7. dry with materialdried over sodium sulfate
8. filtrationfiltered

ORD record

ord-011ad9f21fa945af8c08eaf2d1cd81d8

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569302B2