Styrene → 1,1-Diphenylethane

HRID 2166319Notes

Reaction equation

HRID 2166319 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C1C=CC=CC=1>[C:3]1([CH:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH3:1])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 7501Styrene

Product 1

HCID 119181,1-DiphenylethaneYield 25%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

One known synthesis of this odorant is based on the Friedel-Crafts reaction of styrene with benzene (see Spilker and Schade, Chem. Berichte, 65 (1932), 1686. The product 1,1-diphenylethane was obtained in only 25% yield. Other procedures described in the literature, for example the reaction of benzyl chloride with toluene and cupric chlorides as catalysts (U.S. Pat. No. 3,679,760) or the oxidative coupling of ethylbenzene and benzene with a catalyst consisting of aluminum and cupric chlorides (U.S. Pat. No. 3,631,211) produce only low yields and/or require costly starting materials, so that industrial use is not practical.

Workup

  1. customsynthesis of this odorant

Sources & evidence

ORD record
ord-464d113fb9174d16914457d5bf57731e
Source dataset
uspto-grants-1990_07
Patent number
US04944848

Reaction notes

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