2-Methyl-5-nitrobenzoic acid → (2-Methyl-5-nitrophenyl)methanol

HRID 1946343

Reaction equation

HRID 1946343 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4](O)=[O:5]>C1COCC1.CO>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 1

HCID 5196832-Methyl-5-nitrobenzoic acid

Product 1

HCID 3567085(2-Methyl-5-nitrophenyl)methanolYield 114.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-methyl-5-nitrobenzoic acid (3.0 g, 16.6 mmol, Acros) in THF (60 ml) at ambient temperature under nitrogen was added dropwise 1.0 M borane-tetrahydrofuran complex (33.1 ml, 33.1 mmol, Aldrich). The solution was heated to 80° C. for 1.5 h. To the solution at ambient temperature was slowly added methanol (20 ml) and then heated to 80° C. for 30 min. The solvent was removed in vacuo to leave an oil. The residue was dissolved in methanol (approximately 30 ml) and the solvent removed in vacuo to give (2-methyl-5-nitrophenyl)methanol as a yellow solid (3.18 g).

Workup

  1. customat ambient temperature
  2. temperatureheated to 80° C. for 30 min
  3. customThe solvent was removed in vacuo
  4. customto leave an oil
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a27c82ea6a4045009aa1b2b79a3bb9cd
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Linked notes

Loading…