p-Tolylacetic acid → HCID 13331672, compound

HRID 1274259Notes

Reaction equation

HRID 1274259 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:1][CH2:2][CH2:3][CH3:4])=[O:10])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 248474p-Tolylacetic acid

Product 1

HCID 13331672HCID 13331672, compoundYield 176.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-methylphenylacetic acid (20.6 g, 137 mmol) in methylene chloride (100 mL) in a pressure flask cooled on a dry-acetone bath was added isobutene (190 mL) followed by concentrated sulfuric acid (2.5 mL). After 36 hours, the mixture was cooled (dry ice/acetone bath) and isobutene was removed in a slow stream of nitrogen. The residue was treated with 10% NaHCO3, and extracted with methylene chloride (3×100 mL). The combined methylene chloride extract was washed with 10% NaHCO3 and brine, and dried (Na2SO4). Evaporation of the solvent gave t butyl 4-methylphenylacetate as a colorless oil (25 g, 90%).

Workup

  1. customa dry-acetone bath
  2. additionwas added isobutene (190 mL)
  3. temperaturethe mixture was cooled (dry ice/acetone bath) and isobutene
  4. customwas removed in a slow stream of nitrogen
  5. additionThe residue was treated with 10% NaHCO3
  6. extractionextracted with methylene chloride (3×100 mL)
  7. extractionThe combined methylene chloride extract
  8. washwas washed with 10% NaHCO3 and brine
  9. dry with materialdried (Na2SO4)
  10. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f84b93f96dd3476eb7d2bc9866d734a1
Source dataset
uspto-grants-2000_12
Patent number
US06156784

Reaction notes

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