Hydrochloric Acid → 3-Methyl-2-nitrobenzenemethanol

HRID 862580Notes

Reaction equation

HRID 862580 reaction equation
C[C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9]C)=O.[BH4-].[Na+].[CH3:17]O.Cl>C1COCC1>[CH3:17][C:4]1[C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=[CH:2][CH:3]=1)[CH2:7][OH:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3314122Methyl 5-methyl-2-nitrobenzoateHCID 4311764Sodium borohydride

Product 1

HCID 5619893-Methyl-2-nitrobenzenemethanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a refluxed solution of methyl 5-methyl-2-nitrobenzoate (50 g, 0.256 mol) and sodium borohydride (29 g, 0.768 mol) in THF (400 mL) was added dropwise methanol (60 mL) over 2.5 h. After the addition was completed, the mixture was refluxed for 1 h and allowed to cool at room temperature. The excess reagent was decomposed by addition of diluted hydrochloric acid (300 mL) and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give 43.0 g of the title compound (100%).

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed for 1 h
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2edc453d54e8451783374ba4e7549129
Source dataset
uspto-grants-1998_02
Patent number
US05719152

Reaction notes

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