Phenol → Xanthydrol

HRID 1657622Notes

Reaction equation

HRID 1657622 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

According to the above 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 treating with acid for example polyphosphoric acid. The resulting xanthone is reduced, for example using sodium amalgam in ethanol, to give the xanthydrol.

Sources & evidence

ORD record
ord-5a8a360093064fdbbb5ba97613ad2482
Source dataset
uspto-grants-1976_06
Patent number
US03961069

Reaction notes

Loading…