p-Toluenesulfonic acid → 1-Bromo-2-(1-propen-1-yl)benzene
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8](O)[CH2:9][CH3:10].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][CH3:10]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
With the exception of three compounds, the styrene compounds disclosed herein to be utilized for preparing the α-chloro oximes ae known and their preparations are published in the prior art. The compounds not previously prepared are synthesized following well-known published procedures. Thus, 2-bromobenzaldehyde is allowed to react with a Grignard reagent, ethyl magnesium bromide in anhydrous ether, to yield 1(2-bromophenyl)propanol. This propanol derivative is then dehydrated by refluxing it in toluene in the presence of a catalytic quantity of p-toluenesulfonic acid to yield the desired 1-bromo-2-(1-propenyl)benzene. Another previously unknown substituted styrene, namely, 1,2-dichloro-4-(1-propenyl) benzene is prepared by the same general procedure from 3,4-dichlorobenzaldehyde and ethyl magnesium bromide, followed by dehydration of the intermediate substituted propanol.
Sources & evidence
- ORD record
- ord-d19b66d84483479281f01c3bd59b9e40
- Source dataset
- uspto-grants-1980_04
- Patent number
- US04199525
Reaction notes
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