Hydroquinone → Diphenyl carbonate

HRID 1077609Notes

Reaction equation

HRID 1077609 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[C:9]([O-:12])(=[O:11])C.[Ce+3].C([O-])(=O)C.C([O-])(=O)C.[C:22]1([CH:29]=[CH:28][C:26](O)=[CH:25][CH:24]=1)O>[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[C:9](=[O:11])([O:12][C:22]1[CH:29]=[CH:28][CH:26]=[CH:25][CH:24]=1)[O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 785HydroquinoneHCID 996PhenolHCID 21441352HCID 21441352, compound

Product 1

HCID 7597Diphenyl carbonateYield 23.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 2724163Tetraphenylphosphonium BromideCatalyst

Procedure

The same operation as that in Example 1 was performed using 3.1 g (33 mmol) of phenol, 25.5 mg (0.012 mmol Pd) of 5%-palladium/carbon, 4.0 mg (0.012 mmol) of cerium (III) acetate monohydrate, 101 mg (0.24 mmol) of tetraphenylphosphonium bromide and 13 mg (0.12 mmol) of hydroquinone. After reaction for 3 hours, diphenyl carbonate was obtained with a yield of 23.7% (3.9 mmol). Phenyl salicylate and p-phenoxyphenol were produced as by-products with yields of 0.55% (0.090 mmol) and 0.15% (0.025 mmol), respectively. The selectivity of p-phenoxyphenol was 0.6%.

Workup

  1. customAfter reaction for 3 hours

Sources & evidence

ORD record
ord-11ede1b21198470cba4791639194e7f5
Source dataset
uspto-grants-1996_08
Patent number
US05543547

Reaction notes

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