Bromide ion → Diphenyl carbonate

HRID 654578Notes

Reaction equation

[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]1([O:14][C:15]2C=CC=CC=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1(=O)C=CC(=[O:27])C=C1.[Br-].O=O.C(=O)=O.[C]=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C([O-])(=O)C.[Co+2].C([O-])(=O)C>[C:15](=[O:27])([O:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Procedure of Example 1 was repeated except there was utilized 50.1 grams of phenol, 6.281 grams of diphenyl ether, 1.955 grams of benzoquinone, 1.5 gram of tetraabutylammonium bromide, 0.060 of palladium (II) acetate and 0.032 gram of cobalt (II) acetate. The reactor was sealed and pressurized with 400 psi of oxygen, 450 psi of carbon dioxide, and 800 psi of carbon monoxide to provide a total pressure of 1650 psi at room temperature. The reactor was heated to 100° C. At 0.5 hours, the pressure of the reactor was reduced to 1200 psi and then repressurized with 400 psi of oxygen and 600 psi of carbon monoxide. After 1 hour, the pressure of the reactor was reduced to 1000 psi, then repressurized with 350 psi of oxygen and 700 psi of carbon monoxide. The aforementioned repressurizing procedure was repeated after 2 hours had elapsed. At this time, a sample of the reaction mixture showed that it contained 22% yield of diphenyl carbonate based on GC. After the reaction had been running for 5 hours the mixture showed that it contained 14.85 grams or a 26.1% yield of diphenyl carbonate.

Workup

customThe reactor was sealed
customto provide a total pressure of 1650 psi at room temperature
waitAfter 1 hour
waitThe aforementioned repressurizing procedure was repeated after 2 hours

Sources & evidence

ORD record: ord-0057dbd5d466430c8e089d9f49fd2586
Source dataset: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05132447

Reaction notes

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