Triethylamine → 4-(Methoxycarbonyl)-2,6-dimethylbenzoic acid

HRID 1058454Notes

Reaction equation

HRID 1058454 reaction equation
FC(F)(F)S(O[C:7]1[C:12]([CH3:13])=[CH:11][C:10]([C:14]([O:16][CH3:17])=[O:15])=[CH:9][C:8]=1[CH3:18])(=O)=O.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[C]=O.[C:59]([O:62]CC)(=[O:61])C>C(#N)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:18][C:8]1[CH:9]=[C:10]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[C:12]([CH3:13])[C:7]=1[C:59]([OH:62])=[O:61]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 11849880Methyl 3,5-dimethyl-4-(((trifluoromethyl)sulfonyl)oxy)benzoateHCID 178418416HCID 178418416, compound

Product 1

HCID 3482914-(Methoxycarbonyl)-2,6-dimethylbenzoic acid

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of trifluoromethanesulfonic acid, 4-(methoxycarbonyl)-2,6-dimethylphenyl ester (3.12 g, 10 mmol) in acetonitrile (80 mL) and water (10 mL) at 25° C. is added palladium (II) acetate (224.5 mg, 1.0 mmol), 1,3-bis(diphenylphosphino)propane (412.5 mg, 10 mmol), followed by triethylamine (2.79 mL, 20 mmol). The reaction is then pressurized to 40 psi with carbon monoxide and heated to 80° C. for 4 h. The mixture is diluted with ethyl acetate (500 mL) and is washed with water (250 mL) containing 5 mL of triethylamine. The separated aqueous layer is re-extracted with ethyl acetate (2×250 mL) and the combined organic layers are discarded. The aqueous phase is then adjusted with 1N hydrochloric acid solution to pH 2 and is extracted with ethyl acetate (500 mL). The organic extract is washed with water (250 mL) and brine (250 mL), then is dried (MgSO4), filtered and evaporated in vacuo to yield 2,6-dimethyl-4-(methoxycarbonyl)benzoic acid.

Workup

  1. washis washed with water (250 mL)
  2. additioncontaining 5 mL of triethylamine
  3. extractionThe separated aqueous layer is re-extracted with ethyl acetate (2×250 mL)
  4. extractionis extracted with ethyl acetate (500 mL)
  5. extractionThe organic extract
  6. washis washed with water (250 mL) and brine (250 mL)
  7. dry with materialis dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-403c1cf83aea4d7fbfcb9293d790660f
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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