4-Methyl-2-nitrobenzoic acid → (4-Methyl-2-nitrophenyl)methanol

HRID 2060050Notes

Reaction equation

HRID 2060050 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1>O1CCCC1>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

Participants

3

Reactant 1

HCID 2550274-Methyl-2-nitrobenzoic acid

Product 1

HCID 53405041(4-Methyl-2-nitrophenyl)methanolYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-methyl-2-nitrobenzoic acid (5 g, 27.6 mmol) in tetrahydrofuran (THF) (27 mL) was added borane tetrahydrofuran complex (35.9 mL, 35.9 mmol) and the mixture stirred at reflux for 3 hours. After cooling, the reaction mixture was extracted with water and DCM. The combined organic layers were dried over MgSO4 and then evaporated to dryness to give the alcohol (D139) as a pale yellow solid (4.52 g, 98%) which was used without further purification.

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureAfter cooling
  3. extractionthe reaction mixture was extracted with water and DCM
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-199e3ed29ba74c329d60617fec0f9f74
Source dataset
uspto-grants-2012_10
Patent number
US08278328B2

Reaction notes

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