Sodium borohydride → [3-(3-Chloro-phenoxy)-4-methoxy-phenyl]-methanol

HRID 332575

Reaction equation

HRID 332575 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH:9]=[O:10].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][C:6]1[CH:7]=[C:8]([CH2:9][OH:10])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 577011293-(3-Chloro-phenoxy)-4-methoxy-benzaldehyde

Product 1

HCID 57701122[3-(3-Chloro-phenoxy)-4-methoxy-phenyl]-methanolYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(3-chloro-phenoxy)-4-methoxy-benzaldehyde (12) (393 mg, 1.5 mmol) in methanol (5 ml) was added sodium borohydride (300 mg, 7 mmol) at 0° C. The reaction mixture was stirred at room temperature for 16 h. The mixture was poured into ice-water, extracted with ethyl acetate, washed with water and brine, and dried over Na2SO4. The solvent was removed under vacuum to yield 330 mg (85% yield) of compound (13).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-dc4d906e03ec4a2cbd4c288def7a4b6f
Source dataset
uspto-grants-2014_11
Patent number
US08877816B2

Linked notes

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