Water → (2-Chloro-3-nitrophenyl)methanol

HRID 1861926Notes

Reaction equation

HRID 1861926 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].O>O1CCCC1>[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 962WaterHCID 198702-Chloro-3-nitrobenzoic acid

Product 1

HCID 15132843(2-Chloro-3-nitrophenyl)methanolYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A borane-tetrahydrofuran complex (1.0 M, 20 ml) was added dropwise to a solution of 2-chloro-3-nitrobenzoic acid (5.0 g) in anhydrous tetrahydrofuran (30 ml) in a nitrogen atmosphere and the mixture was heated under reflux for 16 h. Water was added to the reaction mixture which was extracted with ethyl acetate; the organic layer was washed successively with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, dried with anhydrous-sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=5:2) to give 3.5 g of the titled compound (yield, 84%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 16 h
  3. extractionwas extracted with ethyl acetate
  4. washthe organic layer was washed successively with a saturated aqueous sodium bicarbonate solution
  5. dry with materiala saturated aqueous sodium chloride solution, dried with anhydrous-sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=5:2)

Sources & evidence

ORD record
ord-f131ef60c4334699bee41e58b2d07cbe
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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