Hydrochloric Acid → HCID 178511251, compound

HRID 1731458Notes

Reaction equation

HRID 1731458 reaction equation
[BH4-].[Na+].[C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH:11]=[O:12])[CH2:7][CH2:6]1)#[N:4].Cl>CO.C(OCC)C>[OH:12][CH2:11][C@H:8]1[CH2:9][CH2:10][C@H:5]([C:3]#[N:4])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 178511250HCID 178511250, compound

Product 1

HCID 178511251HCID 178511251, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 21864698Diethyl ether methanolSolvent2×

Conditions

Temperature
10 °C

Procedure

A suspension of 829 mg of sodium borohydride in 20 ml of methanol/diethyl ether (vol. 9:1) was treated dropwise within 5 minutes at 0° C. with a solution of 3.0 g of trans-4-cyanocyclohexanecarboxaldehyde in 30 ml of methanol/diethyl ether (vol. 9:1). The reaction mixture was stirred for a further 2 hours at 10° C., then treated with 10 ml of dilute hydrochloric acid and partitioned in methylene chloride/water. The aqueous phase was extracted three times with methylene chloride. The organic phases were washed twice with water, dried over magnesium sulphate, filtered and concentrated. There were obtained 3.0 g (98%) of trans-4-(hydroxymethyl)cyclohexanecarbonitrile as a colourless oil.

Workup

  1. custompartitioned in methylene chloride/water
  2. extractionThe aqueous phase was extracted three times with methylene chloride
  3. washThe organic phases were washed twice with water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c8758ecfb2974096b8c2120be66a8a12
Source dataset
uspto-grants-1986_11
Patent number
US04621901

Reaction notes

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