Ethyl 3-phenoxyprop-2-enoate → Ethyl 3-phenoxy-2,2-dichlorocyclopropanecarboxylate

HRID 2049835Notes

Reaction equation

HRID 2049835 reaction equation
[Cl:1][C:2](Cl)([Cl:6])C([O-])=O.[Na+].[O:9]([CH:16]=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>COCCOC>[O:9]([CH:16]1[CH:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:2]1([Cl:6])[Cl:1])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 237844Ethyl 3-phenoxyprop-2-enoateHCID 23681045Sodium Trichloroacetate

Product 1

HCID 20344573Ethyl 3-phenoxy-2,2-dichlorocyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

The mixture of 20.9 g (113 mmol) sodium trichloroacetate, 15.4 g (80 mmol) ethyl 3-phenoxy-2-propenoate and 50 ml dry 1,2-dimethoxyethane is heated under reflux for 10 hr, under nitrogen. The mixture is filtered and solvent removed. The residue is purified by chromatography on silica gel, giving ethyl 3-phenoxy-2,2-dichlorocyclopropanecarboxylate, which is then hydrolyzed, as in Example 3, to give the corresponding carboxylic acid.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 10 hr, under nitrogen
  3. filtrationThe mixture is filtered
  4. customsolvent removed
  5. customThe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-5edbde6d754c417bba407cf40210abf3
Source dataset
uspto-grants-1980_04
Patent number
US04198527

Reaction notes

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