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Hydrochloric Acid → HCID 178418615, compound

HRID 1707906
Notes
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Reaction equation

HRID 1707906 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 887
Methanol
Solvent

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-5f22322bd715443396871309a862d9d7
Source dataset
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05356563

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes