Phenol → Xanthydrol

HRID 1576382Notes

Reaction equation

HRID 1576382 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-phenoxy-benzoic acid is cyclized by treating 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-26db78ca4db94d6dbecc5184e273a875
Source dataset
uspto-grants-1976_09
Patent number
US03980788

Reaction notes

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