Methanol → Methyl 2-(3,4-dimethylphenyl)acetate

HRID 985566Notes

Reaction equation

HRID 985566 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#N)[CH:5]=[CH:6][C:7]=1[CH3:8].[OH:12]S(O)(=O)=O.[CH3:17][OH:18]>O>[CH3:17][O:18][C:10](=[O:12])[CH2:9][C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 764012-(3,4-Dimethylphenyl)acetonitrile

Product 1

HCID 17607842Methyl 2-(3,4-dimethylphenyl)acetateYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture solution of 2-(3,4-dimethylphenyl)acetonitrile (2) (9.395 g, 64.7 mmol) in methanol was refluxed with H2SO4 3.5 ml (64.7 mmol) for 3 days. The mixture was cooled, diluted with H2O and concentrated in vacuo under sodium bicarbonate. The residue was separated H2O and CH2Cl2 and the H2O layer was extracted with CH2Cl2 several times. The combined organic layers were washed with H2O, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with EtOAc/hexanes (1:10) as an eluant to give compound 4.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuo under sodium bicarbonate
  3. customThe residue was separated H2O and CH2Cl2
  4. extractionthe H2O layer was extracted with CH2Cl2 several times
  5. washThe combined organic layers were washed with H2O
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel with EtOAc/hexanes (1:10) as an eluant

Sources & evidence

ORD record
ord-8e13074159644cf9a20d96f227a8b4c2
Source dataset
uspto-grants-2005_03
Patent number
US06872748B2

Reaction notes

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