2-Chloro-3-nitrobenzoic acid → (2-Chloro-3-nitrophenyl)methanol

HRID 335566Notes

Reaction equation

HRID 335566 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]>C1COCC1.O>[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 1

HCID 198702-Chloro-3-nitrobenzoic acid

Product 1

HCID 15132843(2-Chloro-3-nitrophenyl)methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

10.0 g (49.61 mmol) of 2-chloro-3-nitrobenzoic acid are initially charged in 50 ml of THF. With ice cooling, 104 ml of 1M borane/THF complex are added, and the mixture is stirred at RT overnight. At 0° C., the mixture is carefully hydrolyzed using water. After the evolution of gas has ceased, the mixture is diluted with 500 ml of water and the aqueous phase is extracted three times with in total 500 ml of ethyl acetate. The organic phase is washed with saturated sodium chloride solution and dried over magnesium sulfate. The solvent is then removed under reduced pressure using a rotary evaporator. This gives 9.20 g (98% of theory) of the title compound.

Workup

  1. additionWith ice cooling, 104 ml of 1M borane/THF complex are added
  2. customAt 0° C.
  3. extractionthe aqueous phase is extracted three times with in total 500 ml of ethyl acetate
  4. washThe organic phase is washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent is then removed under reduced pressure
  7. customa rotary evaporator

Sources & evidence

ORD record
ord-27b3863d7b224afd81971f4fe4be44b2
Source dataset
uspto-grants-2014_11
Patent number
US08884017B2

Reaction notes

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