Methanol → 2-Methyl-3-nitrobenzyl alcohol

HRID 476527

Reaction equation

HRID 476527 reaction equation
[CH3:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4](OC)=[O:5].[BH4-].[Na+].CO.O>C(O)(C)(C)C>[CH3:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[CH2:4][OH:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 601165Methyl 2-methyl-3-nitrobenzoateHCID 4311764Sodium borohydride

Product 1

HCID 902892-Methyl-3-nitrobenzyl alcoholYield 91.8%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

39.0 g (0.2 mol) of methyl 2-methyl-3-nitrobenzoate was dissolved in 600 ml of tert-butanol, and 19.0 g of sodium borohydride was added thereto. Under refluxing, 150 ml of methanol was dropwise added thereto over a period of 1 hour. The refluxing was continued further for 1 hour to complete the reaction. The reaction mixture was left to cool, and then water was added thereto. The solvent was distilled off under reduced pressure. To the residue, water and chloroform were added, and the organic layer was separated and dried over anhydrous sodium sulfate. Then, the solvent was distilled off to obtain 30.7 g of 2-methyl-3-nitrobenzyl alcohol.

Workup

  1. temperatureUnder refluxing
  2. waitThe refluxing was continued further for 1 hour
  3. customthe reaction
  4. waitThe reaction mixture was left
  5. temperatureto cool
  6. distillationThe solvent was distilled off under reduced pressure
  7. additionTo the residue, water and chloroform were added
  8. customthe organic layer was separated
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThen, the solvent was distilled off

Sources & evidence

ORD record
ord-c8c94b5b103c4b6ea79ec65912403e0d
Source dataset
uspto-grants-1989_12
Patent number
US04885022

Linked notes

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