Methyl chloroformate → Benzoic acid, 4-(1-methylethenyl)-, methyl ester

HRID 362475

Reaction equation

HRID 362475 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([CH3:8])=[CH2:7])=[CH:4][CH:3]=1.[Mg].Cl[C:13]([O:15][CH3:16])=[O:14]>C1COCC1>[C:6]([C:5]1[CH:9]=[CH:10][C:2]([C:13]([O:15][CH3:16])=[O:14])=[CH:3][CH:4]=1)([CH3:8])=[CH2:7]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 743814-Chloro-alpha-methylstyreneHCID 5462224Magnesium

Product 1

HCID 11275336Benzoic acid, 4-(1-methylethenyl)-, methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Preparation of the Grignard compound of 4-chloro-α-methylstyrene by means of Rieke magnesium in THF under reflux and subsequent reaction with 0.95 equivalents of methyl chloroformate at RT. Aqueous working up, extraction with ethyl acetate and column chromatography using cyclohexane/ethyl acetate 85:15 affords methyl 4-isopropenylbenzoate as colorless crystals.

Workup

  1. temperatureunder reflux
  2. extractionextraction with ethyl acetate and column chromatography

Sources & evidence

ORD record
ord-b9804facfb484b00bae18c748b7636e4
Source dataset
uspto-grants-1999_02
Patent number
US05869531

Linked notes

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