Water → 4-(Hydroxymethyl)cyclohexane-1-carbonitrile
Reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][CH:6]([CH:9]=[O:10])[CH2:5][CH2:4]1)#[N:2].[BH4-].[Na+].O>[OH-].[K+]>[OH:10][CH2:9][CH:6]1[CH2:7][CH2:8][CH:3]([C:1]#[N:2])[CH2:4][CH2:5]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
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. while gassing with argon with 378 mg of solid sodium borohydride. After completion of the addition, the mixture was stirred at 0° C. for a further 20 minutes, 50 ml of water were then added and the mixture obtained 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-(hydromethyl)cyclohexanecarbonitrile (chloroform/ethyl acetate 1:1)0.29 (longish spot).
Workup
- additionAfter completion of the addition
- customthe mixture obtained
- extractionwas extracted three times with 50 ml of methylene chloride each time
- washThe organic phases were washed twice with 50 ml of water each time
- dry with materialdried over magnesium sulphate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d286539460b34a94a2e1649c55d2af9d
- Source dataset
- uspto-grants-1988_11
- Patent number
- US04783280
Reaction notes
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