Sodium borohydride → 1-(4-(3-Bromopropyl)phenyl)ethanol

HRID 1170768Notes

Reaction equation

HRID 1170768 reaction equation
[BH4-].[Na+].[Br:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][CH:8]=1>CO>[Br:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([CH:13]([CH3:14])[OH:15])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 148170351-(4-Acetylphenyl)-3-bromopropane

Product 1

HCID 675239911-(4-(3-Bromopropyl)phenyl)ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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. customat about 0 degrees Celsius
  2. customfor about 2 hours

Sources & evidence

ORD record
ord-1107a1ba0ee2402cbeeb9d3848505015
Source dataset
uspto-grants-2010_11
Patent number
US07829155B1

Reaction notes

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