Thionyl Chloride → 1-[3,3-Dimethylbut-1-en-1-yl]-2-nitrobenzene

HRID 656801Notes

Reaction equation

HRID 656801 reaction equation
[CH3:1][C:2]([CH3:16])([CH3:15])[CH:3](O)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12].S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH3:1][C:2]([CH3:16])([CH3:15])[CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 592538163,3-Dimethyl-1-(2-nitrophenyl)butan-2-ol

Product 1

HCID 673970311-[3,3-Dimethylbut-1-en-1-yl]-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 40 g (179 mmol) of 3,3-dimethyl-1-(2-nitrophenyl)butan-2-ol in 400 ml of toluene at room temperature are added 23.44 g (197 mmol) of thionyl chloride, and the mixture is boiled under reflux for 2 h. After washing with 100 ml of saturated sodium bicarbonate solution and distilling the organic phase at 116° C./12 mbar, 20 g (48% of theory) of 1-[(1E)-3,3-dimethylbut-1-en-1-yl]-2-nitrobenzene are obtained.

Workup

  1. temperatureunder reflux for 2 h
  2. washAfter washing with 100 ml of saturated sodium bicarbonate solution
  3. distillationdistilling the organic phase at 116° C./12 mbar, 20 g (48% of theory) of 1-[(1E)-3,3-dimethylbut-1-en-1-yl]-2-nitrobenzene
  4. customare obtained

Sources & evidence

ORD record
ord-2734f25dcf014673b5f77dd91e16e965
Source dataset
uspto-grants-2011_12
Patent number
US08071824B2

Reaction notes

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