Hydrochloric Acid → HCID 59216850, compound

HRID 2245636Notes

Reaction equation

HRID 2245636 reaction equation
C[O:2][C:3](=[O:18])[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][CH2:16][CH3:17].[OH-].[Li+].Cl>O1CCCC1.O>[CH2:16]([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:18])=[O:2])[CH3:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59216851HCID 59216851, compound

Product 1

HCID 59216850HCID 59216850, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

590 mg 2-Ethoxy-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-ethoxy-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-4147c206700a4fe1ac17f792bdc4bcf8
Source dataset
uspto-grants-2010_03
Patent number
US07683181B2

Reaction notes

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