2-Methylbenzenesulfonic acid → 1-(3-Bromopropyl)-4-ethenylbenzene

HRID 1170769Notes

Reaction equation

HRID 1170769 reaction equation
C1(C)C(S(O)(=O)=O)=CC=CC=1.[Br:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([CH3:24])O)=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[Br:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([CH:22]=[CH2:24])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 69252-Methylbenzenesulfonic acidHCID 675239911-(4-(3-Bromopropyl)phenyl)ethanol

Product 1

HCID 184688641-(3-Bromopropyl)-4-ethenylbenzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Also disclosed herein is a method of making 4-vinylbenzenepropanethiol. The method includes providing 1-bromo-3-phenylpropane, adding acetic anhydride and aluminum chloride, incubating the mixture at from about −20 to about 20 degrees Celsius for from about 1 hour to about 12 hours, isolating the resulting p-(3-bromopropyl)acetophenone, adding sodium borohydride to the p-(3-bromopropyl)acetophenone solution in methanol, incubating the mixture at about 0 degrees Celsius for about 2 hours, isolating the resulting p-(3-bromopropyl)-α-methylbenzenemethanol, adding toluensulfonic acid to the solution of p-(3-bromopropyl)-α-methylbenzenemethanol in toluene, refluxing the mixture under inert atmosphere for about 4 hours, isolating the resulting p-(3-Bromopropyl)styrene, adding thiourea to the p-(3-Bromopropyl)styrene, gently refluxing the mixture for about 16 hours, adding sodium hydroxide, and gently refluxing the mixture for about 4 hours.

Workup

  1. temperaturerefluxing the mixture under inert atmosphere for about 4 hours

Sources & evidence

ORD record
ord-b6aa555a935b438d99dcb673c0fe5335
Source dataset
uspto-grants-2010_11
Patent number
US07829155B1

Reaction notes

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