Water → HCID 178509806, compound

HRID 1906332Notes

Reaction equation

HRID 1906332 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[BH4-].[Na+].O.C(OCC)C>C(O)C.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 4311764Sodium borohydrideHCID 157899134-(4-Oxocyclohexyl)benzonitrile

Product 1

HCID 178509806HCID 178509806, compoundYield 6.2%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
-20 °C

Procedure

51.0 g of 4-(p-cyanophenyl)cyclohexanone were almost completely dissolved in 1.5 l of ethanol/water (vol. 4:1) and then treated within 10 minutes with 9.68 g of sodium borohydride. The mixture was stirred for a further 30 minutes and then left to stand overnight. The reaction mixture was subsequently treated cautiously with 350 ml of dilute, ice-cold hydrochloric acid (1 part of concentrated hydrochloric acid to 4 parts of water), then treated with 2 l of water and 1 l of diethyl ether and shaken. The aqueous phase was separated and extracted four times with 0.5 l of diethyl ether each time. The combined organic phases were washed with 100 ml of saturated sodium hydrogen carbonate solution and with 100 ml of saturated sodium chloride solution, dried over sodium sulphate and concentrated. The crude product, which still contained water, was dried further by dissolution in toluene and acetone and concentration. The beige, solid residue (48.9 g) was dissolved in 300 ml of hot toluene and a fine, insoluble residue was filtered off while the mixture was hot. The filtrate was cooled to -20° C. and the crystallizate obtained was filtered off under suction, washed with 50 ml of toluene/hexane (vol. 9:1) and dried. There were thus obtained 31.72 g (61.6%) of pure, light beige trans-4-(p-cyanophenyl)cyclohexanol of m.p. 119.5°-122.4° C. A further 3.21 g (6.2%) of trans-4-(p-cyanophenyl)cyclohexanol of m.p. 116.5°-122.1° C. were obtained from the mother liquor by crystallization from 60 ml of toluene at -20° C.

Workup

  1. waitleft
  2. waitto stand overnight
  3. additionThe reaction mixture was subsequently treated cautiously with 350 ml
  4. additionof dilute
  5. stirringshaken
  6. customThe aqueous phase was separated
  7. extractionextracted four times with 0.5 l of diethyl ether each time
  8. washThe combined organic phases were washed with 100 ml of saturated sodium hydrogen carbonate solution and with 100 ml of saturated sodium chloride solution
  9. dry with materialdried over sodium sulphate
  10. concentrationconcentrated
  11. dry with materialThe crude product, which still contained water, was dried further by dissolution in toluene
  12. concentrationacetone and concentration
  13. dissolutionThe beige, solid residue (48.9 g) was dissolved in 300 ml of hot toluene
  14. filtrationa fine, insoluble residue was filtered off while the mixture
  15. customthe crystallizate obtained
  16. filtrationwas filtered off under suction
  17. washwashed with 50 ml of toluene/hexane (vol. 9:1)
  18. customdried

Sources & evidence

ORD record
ord-e1e0714c44b6468c9964a4a4e85b66fa
Source dataset
uspto-grants-1987_03
Patent number
US04652089

Reaction notes

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