Hydrochloric Acid → 2-METHOXY-4-(TRIFLUOROMETHOXY)BENZOIC ACID

HRID 501235Notes

Reaction equation

HRID 501235 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[O:15][CH3:16].[OH-].[Li+].Cl>O1CCCC1.O>[CH3:16][O:15][C:5]1[CH:6]=[C:7]([O:10][C:11]([F:12])([F:13])[F:14])[CH:8]=[CH:9][C:4]=1[C:3]([OH:17])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57933498HCID 57933498, compound

Product 1

HCID 32589082-METHOXY-4-(TRIFLUOROMETHOXY)BENZOIC ACIDYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

590 mg 2-Methoxy-4-trifluoromethoxy-benzoic acid methyl ester was dissolved in a mixture of 30 ml tetrahydrofuran and 10 ml water. 367 mg lithium hydroxide were added and the reaction mixture stirred at 60° C. for two hours. The cooled reaction mixture was acidified by dropwise addition of concentrated hydrochloric acid, then the mixture was extracted three times with portions of 80 ml ethyl acetate. The combined organic layers were dried over MgSO4. The solvent was removed in vacuo to obtain 518 mg 2-methoxy-4-trifluoromethoxy-benzoic acid.

Workup

  1. customThe cooled reaction mixture
  2. extractionthe mixture was extracted three times with portions of 80 ml ethyl acetate
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5b8e6d6a7630401b9ba474f1fc6284f8
Source dataset
uspto-grants-2010_08
Patent number
US07772257B2

Reaction notes

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