Sodium borohydride → HCID 178521552, compound

HRID 657677Notes

Reaction equation

HRID 657677 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1.[BH4-].[Na+]>CO>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C@H:12]2[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23150298HCID 23150298, compound

Product 1

HCID 178521552HCID 178521552, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-[4-(3-chloropropoxy)phenyl]cyclohexanone (800 mg) in methanol (10 mL) is cooled to a temperature close to 0° C. Sodium borohydride (57 mg) is added and the mixture stirred for one hour at room temperature, then concentrated under reduced pressure. Water (15 mL) is added and the insoluble separated by filtration, rinsed with diethyl ether and dried under reduced pressure to give 550 mg of trans-4-[4-(3-chloropropoxy)phenyl]cyclohexanol as a white solid used without further purification.

Workup

  1. customclose to 0° C
  2. concentrationconcentrated under reduced pressure
  3. additionWater (15 mL) is added
  4. customthe insoluble separated by filtration
  5. washrinsed with diethyl ether
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-48ab2c9832bf4c94b8283dca0a36880c
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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