Water → 4-(Hydroxymethyl)cyclohexane-1-carbonitrile

Temperature

0 °C

A solution of 1.34 g of 4-cyanocyclohexanecarboxaldehyde (cis/trans mixture) in 40 ml of 0.1N methanolic potassium hydroxide solution was treated portionwise at 0° C. under argon gasification with 378 mg of solid sodium borohydride. After completion of the addition, the mixture was stirred at 0° C. for a further 20 minutes, then 50 ml of water were added and the mixture was extracted three times with 50 ml of methylene chloride each time. The organic phases were washed twice with 50 ml of water each time, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.4 bar) of the residual oil on silica gel with chloroform/ethyl acetate (1:1) gave 1.22 g (90%) of 4-(hydroxymethyl)cyclohexanecarbonitrile (likewise as an about 1:1 mixture of the two epimers) as a colourless viscous oil. This material was used in the following tosylation without further purification. Rf-value of 4-(hydroxymethyl)cyclohexanecarbonitrile [chloroform/ethyl acetate (1:1)]: 0.29 (longish spot).

1. additionAfter completion of the addition
2. extractionthe mixture was extracted three times with 50 ml of methylene chloride each time
3. washThe organic phases were washed twice with 50 ml of water each time
4. dry with materialdried over magnesium sulphate
5. concentrationconcentrated

ORD record

ord-b7bf4237e1f34981983be5857dbb7323

Source dataset

uspto-grants-1987_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04708441