Sodium borohydride → (2,6-Dichloro-3-methoxyphenyl)methanol

HRID 2235210Notes

Reaction equation

HRID 2235210 reaction equation
[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[C:6]([Cl:12])[C:3]=1[CH:4]=[O:5].[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[C:6]([Cl:12])[C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 149271732,6-Dichloro-3-methoxybenzaldehyde

Product 1

HCID 21980844(2,6-Dichloro-3-methoxyphenyl)methanolYield 93.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve 2,6-dichloro-3-methoxy-benzaldehyde (10 g, 48.8 mmol) in ethanol (330 ml) add sodiumborohydride (1.8 g, 48.8 mmol) and stir at room temperature over night. Partition reaction mixture between water and ethyl acetate separate layers wash organic with brine, dry over sodium sulfate, filter and concentrate to yield 9.43 g (93%) of (2,6-Dichloro-3-methoxy-phenyl)-methanol.

Workup

  1. customPartition
  2. customreaction mixture between water and ethyl acetate
  3. customseparate layers
  4. washwash organic with brine
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-5126c216c3c74222ac698c14d245ede7
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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