Hydrochloric Acid → HCID 178509804, compound

HRID 622274Notes

Reaction equation

HRID 622274 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([CH:15]=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[BH4-].[Na+].Cl>[OH-].[K+].O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([CH2:15][OH:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 178509803HCID 178509803, compound

Product 1

HCID 178509804HCID 178509804, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

60 g of trans-4-(p-cyanophenyl)cyclohexanecarboxaldehyde were dissolved in 500 ml of 0.1N methanolic potassium hydroxide solution and the solution was treated portionwise within 1 hour at 0° C. with 3.1 g of sodium borohydride. Thereafter, the reaction mixture was diluted with about 200 ml of water and cautiously adjusted to pH 2-3 in an ice-bath with about 40 ml of 25 percent hydrochloric acid. The mixture was extracted with methylene chloride and the organic phase was dried over magnesium sulphate and concentrated. Crystallization from a mixture of 250 ml of ethyl acetate and 250 ml of petroleum ether gave 45.75 g of trans-4-(p-cyanophenyl)-hydroxymethylcyclohexane (purity 99.6%) as colourless crystals with m.p. 108° C.

Workup

  1. extractionThe mixture was extracted with methylene chloride
  2. dry with materialthe organic phase was dried over magnesium sulphate
  3. concentrationconcentrated
  4. customCrystallization
  5. additionfrom a mixture of 250 ml of ethyl acetate and 250 ml of petroleum ether

Sources & evidence

ORD record
ord-bcced46785e74babae66140744385077
Source dataset
uspto-grants-1988_09
Patent number
US04770503

Reaction notes

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