Phenol → Phenyl Salicylate

HRID 1077611Notes

Reaction equation

HRID 1077611 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.C([O-])(=O)C.[Ce+3].C([O-])(=O)C.C([O-])(=O)C.[Br-].[Cs+].[C]=O.[C:26](=O)([O:34]C1C=CC=CC=1)[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>[Pd]>[C:26]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:34])[C:2]1[C:1](=[CH:6][CH:5]=[CH:4][CH:3]=1)[OH:7]

Participants

7

Reactant 5

HCID 996PhenolHCID 7597Diphenyl carbonateHCID 24592Cesium bromide (CsBr)HCID 21441352HCID 21441352, compoundHCID 178418416HCID 178418416, compound2×

Product 1

HCID 8361Phenyl Salicylate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst2×

Procedure

3.0 g (32 mmol) of phenol, 25.8 mg (0.012 mmol Pd) of 5%-palladium/carbon, 4.2 mg (0.012 mmol) of cerium (III) acetate monohydrate, and 5.18 mg (0.24 mmol) of cesium bromide were charged in a 30-ml Hastelloy autoclave. After air in the system was replaced by carbon monoxide, 60 Kg/cm2 of carbon monoxide and 30 Kg/cm2 of dry air were introduced into the autoclave, followed by reaction at 100° C. for 3 hours. As a result of gas chromatographic analysis of the reaction solution, the yield of diphenyl carbonate was 9.4% (1.5 mmol). The yields of phenyl salicylate and p-phenoxyphenol which were produced as by-products were 0.32% (0.05 mmol) and 0.13% (0.02 mmol), respectively. After the completion of reaction, the gas phase contained 0.4% of carbon dioxide.

Workup

  1. additionwere introduced into the autoclave
  2. customfollowed by reaction at 100° C. for 3 hours
  3. customAs a result of gas chromatographic analysis of the reaction solution

Sources & evidence

ORD record
ord-20b3fb0d27bf4ab2a44cf7416d9449ae
Source dataset
uspto-grants-1996_08
Patent number
US05543547

Reaction notes

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