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

HRID 1621027Notes

Reaction equation

HRID 1621027 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 introduced into 100 ml of THF. While cooling in ice, 109 nil of 1 M borane-THF complex are added, and the mixture is stirred at room temperature overnight. It 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 immediately reacted further.

Workup

  1. temperatureWhile cooling in ice
  2. addition109 nil of 1 M borane-THF complex are added
  3. concentrationIt 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 immediately reacted further

Sources & evidence

ORD record
ord-5a42949e1d164e67a084ccff12e842f5
Source dataset
uspto-grants-2014_07
Patent number
US08772511B2

Reaction notes

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