Hydrochloric Acid → 3-(Methoxycarbonyl)-4-methylbenzoic acid

HRID 1820272Notes

Reaction equation

HRID 1820272 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[CH:12]1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:41](=[O:44])([O-])[O-:42].[K+].[K+].[C]=O.Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CO>[CH3:12][O:42][C:41]([C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6])=[O:44]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 821303-Bromo-4-methylbenzoic acidHCID 178418416HCID 178418416, compound

Product 1

HCID 220698023-(Methoxycarbonyl)-4-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolvent

Procedure

A parr reactor was charged with 3-bromo-4-methylbenzoic acid, MeOH (50 mL), palladium acetate (0.44 g, 1.95 mmol), bis(1,3-diphenylphosphino)propane, and potassium carbonate (4.0 g, 29.3 mmol) was pressurized to 80 psi with carbon monoxide gas. The reaction was maintained at this temperature for 48 h. The reaction was cooled, acidified with 1 N HCl, and extracted with methylene chloride. The organic extracts were dried over sodium sulfate, filtered, concentrated and then purified by reverse phase HPLC to yield the title compound.

Workup

  1. temperatureThe reaction was maintained at this temperature for 48 h
  2. temperatureThe reaction was cooled
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-fde10c4914a546c0a2244b88e8a80337
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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