Potassium tert-butoxide → 1-(Chloromethyl)-2-ethenylbenzene

HRID 2708

Reaction equation

HRID 2708 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10]OS(C)(=O)=O.CC(C)([O-])C.[K+]>CCOCC>[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]=[CH2:10]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 54328826Methanesulfonic acid 2-(2-chloromethyl-phenyl)-ethyl ester

Product 1

HCID 897571-(Chloromethyl)-2-ethenylbenzeneYield 82%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-35 °C

Procedure

Dissolve methanesulfonic acid 2-(2-chloromethyl-phenyl)-ethyl ester (8.8 g, 35.4 mmol) in ether (80 mL) and cool to -35° C. Add potassium t-butoxide (10 g, 89 mmol) and stir for 30 minutes. Add water (50 mL) and ether (150 mL), extract, dry (Na2SO4) and purify by silica gel chromatography (2:3 methylene chloride/pentane) to give 1-chloromethyl-2-vinyl-benzene as a colorless oil (4.43 g, 82%).

Workup

  1. extractionAdd water (50 mL) and ether (150 mL), extract
  2. dry with materialdry (Na2SO4)
  3. custompurify by silica gel chromatography (2:3 methylene chloride/pentane)

Sources & evidence

ORD record
ord-fc7f4a6b6ae94decb6730375d9ad1be0
Source dataset
uspto-grants-1998_03
Patent number
US05731306

Linked notes

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