Sodium borohydride → HCID 86703636, compound

HRID 1849754Notes

Reaction equation

HRID 1849754 reaction equation
[Cl:1][C:2]1([Cl:9])[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.[BH4-].[Na+]>CO>[Cl:1][C:2]1([Cl:9])[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67193005HCID 67193005, compound2×

Product 1

HCID 86703636HCID 86703636, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a mixture of 4,4-dichlorocyclohexanone (WO2011/006794A 1) (5.20 g, 31.10 mmol) in anhydrous methanol (100 mL) was added sodium borohydride (2.35 g, 62.20 mmol) at 0° C. The reaction mixture was allowed to warm to ambient temperature and stirred for 1 hour. Concentration in vacuo yielded a residue which was re-dissolved in methanol (50 mL) and concentrated again in vacuo. The residue was then purified by silica gel column chromatography using 10-100% ethyl acetate in hexanes as eluent to afford 4,4-dichlorocyclohexanol as an orange solid (1.90 g, 36%).

Workup

  1. concentrationConcentration in vacuo
  2. customyielded a residue which
  3. concentrationconcentrated again in vacuo
  4. customThe residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b58f3a68efb54c0b8c449d2da59bae4e
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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