Hydrochloric Acid → HCID 21105730, compound

HRID 1354420Notes

Reaction equation

HRID 1354420 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]3[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=3[C:16]([O:18]CC)=[O:17])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[OH-].[Na+].O1CCCC1.Cl>O.C(O)C>[F:25][C:2]([F:1])([F:26])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][C:12]([C:14]3[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=3[C:16]([OH:18])=[O:17])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22934574HCID 22934574, compound

Product 1

HCID 21105730HCID 21105730, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 2-[5-(4-trifluoromethylphenyl)-2-furyl]benzoate (1.80 g), 1 M aqueous sodium hydroxide solution (20 ml), tetrahydrofuran (35 ml) and ethanol (35 ml) was stirred at 60° C. for 1 hr. After cooling, the reaction mixture was poured into water and 1 M hydrochloric acid (30 ml) was added. The mixture was extracted with ethyl acetate-tetrahydrofuran (1:1, volume ratio). The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from hexane-ethanol to give 2-[5-(4-trifluoromethylphenyl)-2-furyl]benzoic acid (1.15, yield 53%) as colorless plate crystals. melting point: 182–183° C.

Workup

  1. temperatureAfter cooling
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate-tetrahydrofuran (1:1, volume ratio)
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was recrystallized from hexane-ethanol

Sources & evidence

ORD record
ord-880eca8120a9429ba4ecb2175f2ccb15
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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