Water → HCID 12784820, compound

HRID 2412464Notes

Reaction equation

HRID 2412464 reaction equation
[Cl:1][C:2]([Cl:15])=[CH:3][CH:4]([CH3:14])[CH:5]([CH:11]1[CH2:13][CH2:12]1)[C:6]([O:8]CC)=[O:7].[OH-].[Na+].O.C([O-])(=O)CC([O-])=O>C(O)C>[Cl:1][C:2]([Cl:15])=[CH:3][CH:4]([CH3:14])[CH:5]([CH:11]1[CH2:12][CH2:13]1)[C:6]([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 9084Malonate IonHCID 14798Sodium HydroxideHCID 13227594HCID 13227594, compound

Product 1

HCID 12784820HCID 12784820, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 500 ml flask was equipped with a magnetic stirrer and a reflux condenser with a nitrogen inlet. The flask was charged with 57.0 g (0.227 mol) of ethyl 5,5-dichloro-3-methyl-2-cyclopropyl-4-pentenoate, 27.24 g (0.681 mol) of sodium hydroxide, 97 ml of water, and 97 ml of ethanol. The reaction mixture was refluxed for four days. After cooling to room temperature, most of the ethanol was removed on the rotary evaporator, the residue diluted with water and extracted twice with ether. The aqueous layer was acidified with concentrated hydrochloric acid, and extracted three times with ether. The combined ether extracts were washed twice with water, dried (MgSO4), and the solvent removed to leave 45.82 g (90% yield) of a honey colored oil.

Workup

  1. customA 500 ml flask was equipped with a magnetic stirrer and a reflux condenser with a nitrogen inlet
  2. temperatureThe reaction mixture was refluxed for four days
  3. customwas removed on the rotary evaporator
  4. additionthe residue diluted with water
  5. extractionextracted twice with ether
  6. extractionextracted three times with ether
  7. washThe combined ether extracts were washed twice with water
  8. dry with materialdried (MgSO4)
  9. customthe solvent removed

Sources & evidence

ORD record
ord-bc945df9ebab4c8fb831f3e5922451dc
Source dataset
uspto-grants-1985_01
Patent number
US04492799

Reaction notes

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