Thionyl Chloride → 2,4-Bis(1,1-dimethylethyl)-1-(2-chloroethyl)benzene

HRID 37630Notes

Reaction equation

HRID 37630 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[CH2:15][CH2:16]O)([CH3:4])[CH3:3].S(Cl)([Cl:20])=O>C1(C)C=CC=CC=1>[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[CH2:15][CH2:16][Cl:20])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 199360802,4-Bis(1,1-dimethylethyl)benzeneethanol

Product 1

HCID 199360882,4-Bis(1,1-dimethylethyl)-1-(2-chloroethyl)benzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of the title product of Example 10 (2.0 grams, 8.5 mmoles) and thionyl chloride (2.03 g, 17.1 mmoles) in toluene (50 ml) is heated at reflux for one hour. After cooling, the mixture is evaporated. Chromatography of the residue over silica gel using mixtures of ethyl acetate and hexane as eluents gives the title compound.

Workup

  1. temperatureat reflux for one hour
  2. temperatureAfter cooling
  3. customthe mixture is evaporated

Sources & evidence

ORD record
ord-638fa1b3a63b4d41a64405713e7c3986
Source dataset
uspto-grants-1995_05
Patent number
US05420343

Reaction notes

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