Pyridine → 1-Chloro-1-(p-prenylphenyl)ethane

HRID 1413831Notes

Reaction equation

HRID 1413831 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([CH:12](O)[CH3:13])=[CH:8][CH:7]=1)[CH:2]=[C:3]([CH3:5])[CH3:4].N1C=CC=CC=1.S(Cl)([Cl:23])=O>C1C=CC=CC=1>[Cl:23][CH:12]([C:9]1[CH:10]=[CH:11][C:6]([CH2:1][CH:2]=[C:3]([CH3:5])[CH3:4])=[CH:7][CH:8]=1)[CH3:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 132172751-(p-Prenylphenyl)ethanol

Product 1

HCID 132919731-Chloro-1-(p-prenylphenyl)ethaneYield 97.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 9.5 g of 1-(p-prenylphenyl)-ethanol, 4.0 ml of pyridine and 60 ml of benzene, a solution of 5.9 g of thionyl chloride in 10 ml of benzene was added dropwise at 0°-5° C. with stirring. After stirring at room temperature for an hour, the reaction mixture was washed with water, aqueous sodium hydrogen carbonate and water successively and dried. Removal of the benzene gave 10.1 g of 1-chloro-1-(p-prenylphenyl)ethane.

Workup

  1. stirringAfter stirring at room temperature for an hour
  2. washthe reaction mixture was washed with water, aqueous sodium hydrogen carbonate and water successively
  3. customdried
  4. customRemoval of the benzene

Sources & evidence

ORD record
ord-786247acd8e441f597923049a809feea
Source dataset
uspto-grants-1981_02
Patent number
US04251543

Reaction notes

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