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

HRID 1691614Notes

Reaction equation

HRID 1691614 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 ml 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 ml 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-4680077ad8b841d99a2232909d2addce
Source dataset
uspto-grants-2012_04
Patent number
US08153799B2

Reaction notes

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