Methanol → Methyl 2-(2-methylphenyl)acetate

HRID 1278975Notes

Reaction equation

HRID 1278975 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([OH:10])=[O:9].S(=O)(=O)(O)O.[CH3:17]O>CCCCCC.C(OCC)(=O)C>[C:1]1([CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([O:10][CH3:17])=[O:9]

Participants

6

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 69519o-Tolylacetic acid

Product 1

HCID 7021479Methyl 2-(2-methylphenyl)acetateYield 98%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

30.0 g of o-tolylacetic acid (0.2 mol) was dissolved in 100 ml of methanol, 5 ml of concentrated sulfuric acid was added thereto and the resulting solution was stirred with heating for 6 to 12 hours. The resulting solution was cooled and the solvent was removed under a reduced pressure to obtain a residue. The residue was washed twice with water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and the solvent was removed under a reduced pressure. The residue thus obtained was subjected to column chromatography using a mixture of n-hexane and ethyl acetate (4:1) as an eluent to obtain 32.15 g (yield 98%) of the title compound as a colorless liquid.

Workup

  1. temperaturewith heating for 6 to 12 hours
  2. temperatureThe resulting solution was cooled
  3. customthe solvent was removed under a reduced pressure
  4. customto obtain a residue
  5. washThe residue was washed twice with water
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. customthe solvent was removed under a reduced pressure
  9. customThe residue thus obtained

Sources & evidence

ORD record
ord-b712ce3cb36e488e9f52d109a4cd7a10
Source dataset
uspto-grants-2002_09
Patent number
US06444850B1

Reaction notes

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