3-Bromobenzaldehyde → 3-Bromobenzyl alcohol

HRID 657347Notes

Reaction equation

HRID 657347 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[O:8]>CCO>[Br:3][C:4]1[CH:5]=[C:6]([CH2:7][OH:8])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 765833-BromobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 851413-Bromobenzyl alcoholYield 99.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (7.1 g, 186.1 mmol) in several portions was added to a solution of 3-bromobenzaldehyde (114.8 g, 620.4 mmol) in EtOH (650 mL) at 25° C. Then the mixture was stirred for 1 h at room temperature. The reaction was quenched with water (200 mL). After removing EtOH, the residue was dissolved in AcOEt (500 mL), and filtered. The filtrate was washed with water (150 mL), brine (150 mL), and dried over Na2SO4. After removing the solvent, 115.8 g of the title compound was obtained (yield: 99.8%).

Workup

  1. customThe reaction was quenched with water (200 mL)
  2. customAfter removing EtOH
  3. dissolutionthe residue was dissolved in AcOEt (500 mL)
  4. filtrationfiltered
  5. washThe filtrate was washed with water (150 mL), brine (150 mL)
  6. dry with materialdried over Na2SO4
  7. customAfter removing the solvent

Sources & evidence

ORD record
ord-a6df00b9960a408aacde8fbedd51f757
Source dataset
uspto-grants-2011_12
Patent number
US08071588B2

Reaction notes

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