Phenol → Xanthydrol

HRID 1605146Notes

Reaction equation

HRID 1605146 reaction equation
C1(O)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[O:14]([C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](O)=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1C2C(=O)C3C(=CC=CC=3)OC=2C=CC=1>C(O)C.[Cu].[Na].[Hg]>[CH:18]1[CH:19]=[C:20]2[CH:23]([OH:24])[C:22]3[C:21]([O:14][C:15]2=[CH:16][CH:17]=1)=[CH:29][CH:28]=[CH:27][CH:26]=3

Participants

8

Reactant 4

HCID 996PhenolHCID 7020XanthoneHCID 11430Potassium CarbonateHCID 752372-Phenoxybenzoic acid

Product 1

HCID 72861Xanthydrol

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 9837419Sodium amalgamCatalystHCID 702EthanolSolvent

Procedure

The xanthydrols are either known to the art or are prepared by the following procedure. A 2-halobenzoic acid is reacted with a phenol preferably in the presence of a base such as potassium carbonate and in the presence of cuprous iodide and copper bronze. The resulting 2-phenoxybenzoic acid is cyclized by reacting with acid for example polyphosphoric acid. The resulting xanthone is reduced, for example using sodium amalgam in ethanol, to give the xanthydrol.

Workup

  1. customare prepared by the following procedure

Sources & evidence

ORD record
ord-49ad4d73ed9a44eab7c52ce0e2d6262b
Source dataset
uspto-grants-1976_04
Patent number
US03949076

Reaction notes

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