Ammonium Chloride → cis-5-Hydroxy-2,2-dimethylcyclohexanecarbonitrile

Under a nitrogen atmosphere, a solution of 2,2-dimethyl-5-oxocyclohexanecarbonitrile (4.0 g, 0.0265 mol) in methanol (30 ml) was added dropwise to a solution of sodium borohydride (1.00 g, 0.0265 mol) in methanol (40 ml) at 0° C. After 1 hour, sodium borohydride (0.0133 mol) was further added thereto and the resulting mixture was warmed up to room temperature. After 45 minutes, a saturated aqueous ammonium chloride solution was added to the reaction solution and then the methanol was concentrated under reduced pressure. The resulting aqueous solution was diluted with water and extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain cis-5-hydroxy-2,2-dimethylcyclohexanecarbonitrile (3.0550 g, 75%).

1. waitAfter 45 minutes
2. concentrationthe methanol was concentrated under reduced pressure
3. additionThe resulting aqueous solution was diluted with water
4. extractionextracted with chloroform
5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
6. customThe organic layer dried
7. concentrationwas concentrated under reduced pressure
8. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

ORD record

ord-9cd9849522a14908be0f27415ac4f6ba

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07199147B2