Styrene → 1-(2-Bromophenyl)-1-propanol

HRID 2049956Notes

Reaction equation

HRID 2049956 reaction equation
[CH2:1]=[CH:2]C1C=CC=CC=1.[Br:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=[O:13].C([Mg]Br)C>CCOCC>[Br:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]([OH:13])[CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 7501StyreneHCID 811292-BromobenzaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 134442791-(2-Bromophenyl)-1-propanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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.

Workup

  1. customThe compounds not previously prepared
  2. customare synthesized

Sources & evidence

ORD record
ord-14bbe3e347e347249d146f3f90ecbbd0
Source dataset
uspto-grants-1980_04
Patent number
US04199525

Reaction notes

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