4-Nitrosalicylic acid → 2-Hydroxy-4-nitrobenzyl alcohol

HRID 15445Notes

Reaction equation

HRID 15445 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:13])[C:7](=[CH:11][CH:12]=1)[C:8](O)=[O:9])([O-:3])=[O:2]>C1COCC1>[OH:9][CH2:8][C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=1[OH:13]

Participants

3

Reactant 1

HCID 692664-Nitrosalicylic acid

Product 1

HCID 118160942-Hydroxy-4-nitrobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10.0 g (54.6 mmol) of 4-nitrosalicylic acid are initially charged in 100 ml of THF. With ice-cooling, 109 ml of 1 M borane/THF complex are added, and the mixture is stirred at RT overnight. The mixture is concentrated and the precipitate is filtered off with suction. The solid is dissolved in ethyl acetate and dried over magnesium sulfate. After concentration and drying under high vacuum, the title compound is directly reacted further.

Workup

  1. temperatureWith ice-cooling
  2. addition109 ml of 1 M borane/THF complex are added
  3. concentrationThe mixture is concentrated
  4. filtrationthe precipitate is filtered off with suction
  5. dissolutionThe solid is dissolved in ethyl acetate
  6. dry with materialdried over magnesium sulfate
  7. concentrationAfter concentration
  8. customdrying under high vacuum
  9. customthe title compound is directly reacted further

Sources & evidence

ORD record
ord-13e21c06ca6a44e48ea17cc79316ba5e
Source dataset
uspto-grants-2010_06
Patent number
US07732477B2

Reaction notes

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