Water → Stilbene

HRID 2372544Notes

Reaction equation

HRID 2372544 reaction equation
O.[I-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+].Br[CH:12]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[C:14]1([CH:13]=[CH:12][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 24477Sodium ThiosulfateHCID 93010Benzene, 1,1'-(1,2-dibromo-1,2-ethanediyl)bis-

Product 1

HCID 11502StilbeneYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Hexadecyltributyl phosphonium hectorite (0.050 mmol) was mixed with 2.0 ml of water containing dissolved sodium iodide (0.264 mmol) and sodium thiosulfate (32.0 mmol) and toluene (2.0 ml) containing dissolved 1,2-dibromo-1,2-diphenyl ethane (1.0 mml). After vigorous stirring for a reaction time of 7 hr at 90° C. the emulsion was broken by centrifugation, and 1,2-diphenylethylene was obtained in 98.0% yield.

Workup

  1. additioncontaining

Sources & evidence

ORD record
ord-665a8b49ab934fa88f42b915a76f8c33
Source dataset
uspto-grants-1992_03
Patent number
US05099054

Reaction notes

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