Tetrahydrofuran → HCID 21105764, compound

HRID 1354424Notes

Reaction equation

HRID 1354424 reaction equation
C([O:8][C:9]1[CH:24]=[CH:23][C:22]([C:25]2[O:26][C:27]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=3)=[CH:28][CH:29]=2)=[CH:21][C:10]=1[C:11]([O:13]CC1C=CC=CC=1)=[O:12])C1C=CC=CC=1.O1CCCC1>[Pd].CO>[F:38][C:36]([F:37])([F:39])[C:33]1[CH:32]=[CH:31][C:30]([C:27]2[O:26][C:25]([C:22]3[CH:21]=[C:10]([C:11]([OH:13])=[O:12])[C:9]([OH:8])=[CH:24][CH:23]=3)=[CH:29][CH:28]=2)=[CH:35][CH:34]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 21105765HCID 21105765, compound

Product 1

HCID 21105764HCID 21105764, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 2-benzyloxy-5-[5-(4-trifluromethylphenyl)-2-furyl]benzoate (2.64 g), 5% palladium on carbon (2.6 g), tetrahydrofuran (50 ml) and methanol (50 ml) was stirred under a hydrogen atmosphere at normal pressure and room temperature for 30 min. Palladium on carbon was removed by filtration, and the filtrate was concentrated. The residue was recrystallized from ethanol to give 5-[5-(4-trifluoromethylphenyl)-2-furyl]salicylic acid (1.07 g, yield 62%) as a colorless crystalline powder. melting point: 272–273° C.

Workup

  1. customPalladium on carbon was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-2726fa0fdaea45fbbcb5179a43b8ba56
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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