Ethyl Acetate → 4-Fluoro-3-nitrobenzyl alcohol

HRID 2061125Notes

Reaction equation

HRID 2061125 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][C:5]=1[N+:12]([O-:14])=[O:13].C(OCC)(=O)C>CO.O>[F:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][C:5]=1[N+:12]([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 5981294-Fluoro-3-nitrobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 41675874-Fluoro-3-nitrobenzyl alcoholYield 103.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Sodium borohydride (1.36 g, 35.95 mmol) was added to a solution of 4-fluoro-3-nitrobenzaldehyde (2.0 g, 11.83 mmol) in methanol (15 mL) and water (3.0 mL), and the mixture was stirred at room temperature for 3 hours. Water was then added to the reaction mixture, and extraction was performed with ethyl acetate. The organic extract was washed with saturated saline and dried over magnesium sulfate, and then concentrated under reduced pressure to yield the title compound (2.10 g, 95%) as a pale red oil.

Workup

  1. extractionThe organic extract
  2. washwas washed with saturated saline
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f7bf4c9dd4cb4fbd9b3ba8100a5cd8b2
Source dataset
uspto-grants-2012_10
Patent number
US08278465B2

Reaction notes

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