Dimethyl Sulfoxide → Diphenyl Ether

HRID 1721968Notes

Reaction equation

HRID 1721968 reaction equation
CN([CH:4]=[O:5])C.CS(C)=O.[C:10]1(C)[C:11](C)=[CH:12][CH:13]=[CH:14][CH:15]=1>>[C:15]1([O:5][C:4]2[CH:12]=[CH:11][CH:10]=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 6228DimethylformamideHCID 7237O-Xylene

Product 1

HCID 7583Diphenyl Ether

Procedure

Method G illustrates still another means for obtaining intermediate XIII. In this method, substituted propriolate ester XVI is reacted with amidoxime XVII in a suitable solvent (e.g., alcohol, acetonitrile, THF, dimethylsulfoxide (DMSO), acetone, DMF) at about 0° C. to the reflux temperature of the solvent for about 1-48 hours to obtain olefin XVIII wherein when R1 =H, a mixture of cis and trans isomers is obtained, and when R1 =alkyl or aryl, a mixture of E and Z isomers is obtained. Further treatment of olefin XVIII in solvents such as DMF, DMSO, diphenylether, xylene, and the like, at 0° C. to the reflux temperature of the solvent for about 1-48 hours affords intermediate XIII, preferably for 1 hour in diphenylether at 180°-200° C.

Workup

  1. additiona mixture of cis
  2. customtrans isomers is obtained
  3. customZ isomers is obtained

Sources & evidence

ORD record
ord-a2cfd35f00514594ac190a5ec1c78e50
Source dataset
uspto-grants-1989_08
Patent number
US04853383

Reaction notes

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