Hydrochloric Acid → HCID 178418615, compound

HRID 5302Notes

Reaction equation

HRID 5302 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].C(OCC)C.[BH4-].[Na+].Cl>CO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C@H:15]3[CH2:20][CH2:19][C@H:18]([OH:21])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 4311764Sodium borohydrideHCID 189601524-(4'-Cyano-4-biphenylyl)cyclohexanone

Product 1

HCID 178418615HCID 178418615, compoundYield 34.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 10 g of 4-(4'-cyano-4-biphenylyl)cyclohexanone, 30 ml of diethyl ether and 270 ml of methanol was treated portionwise at 0° C. with 1.8 g of sodium borohydride. After 3 hours the reaction mixture was made acid (pH 1-2) with 25% hydrochloric acid. The reaction mixture was extracted three times with 50 ml of dichloromethane each time. The combined organic phases were washed twice with 500 ml of water each time and subsequently dried over magnesium sulfate, filtered and concentrated. Recrystallization from methanol gave 3.5 g of trans-4-(4'-cyano-4-biphenylyl)cyclohexanol.

Workup

  1. extractionThe reaction mixture was extracted three times with 50 ml of dichloromethane each time
  2. washThe combined organic phases were washed twice with 500 ml of water each time
  3. dry with materialsubsequently dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customRecrystallization from methanol

Sources & evidence

ORD record
ord-d52f08e66fb34664977e68b9daab7854
Source dataset
uspto-grants-1993_09
Patent number
US05244597

Reaction notes

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