Sodium borohydride → [3-(4-Chloro-2-nitro-phenoxy)-phenyl]-methanol

HRID 2197922Notes

Reaction equation

HRID 2197922 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[CH:10]=[O:11])=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH2:10][OH:11])[CH:12]=[CH:13][CH:14]=2)=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 92813413-(4-Chloro-2-nitro-phenoxy)-benzaldehyde

Product 1

HCID 68456706[3-(4-Chloro-2-nitro-phenoxy)-phenyl]-methanolYield 94.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the product from Example 176a (2.0 g. 7.2 mmol) in ethanol (25 mL) was added sodium borohydride (0.32 g, 8.6 mmol). The reaction was stirred for 4 h. The excess sodium borohydride was destroyed by the addition of acetic acid. The reaction was poured into water and extracted with ethyl acetate. The organic layer was separated and washed with water, brine, and dried over sodium sulfate, filtered and concentrated under vacuum giving the title compound (1.9 g, 94%).

Workup

  1. customThe excess sodium borohydride was destroyed by the addition of acetic acid
  2. additionThe reaction was poured into water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1165335a63734cfa82a802118e0fdd81
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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