Hydrochloric Acid → HCID 23317061, compound

HRID 615725Notes

Reaction equation

HRID 615725 reaction equation
[Na].[C:2]([CH:5]([C:11]([CH3:20])([CH3:19])[CH:12](Cl)[CH2:13][C:14]([Cl:17])([Cl:16])[Cl:15])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:4])[CH3:3].Cl>C(O)C>[C:2]([C:5]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:11]([CH3:20])([CH3:19])[CH:12]1[CH2:13][C:14]([Cl:17])([Cl:16])[Cl:15])(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 13646833Ethyl 2-acetyl-4,6,6,6-tetrachloro-3,3-dimethylhexanoate

Product 1

HCID 23317061HCID 23317061, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (0.15 g) was dissolved in 10 ml of absolute ethanol, and 2.29 g of ethyl 2-acetyl-4,6,6,6-tetrachloro-3,3-dimethylhexanoate was added, while the reaction mixture was cooled with ice. After stirring at room temperature for 15 minutes, the mixture was rendered neutral with an ethereal solution of hydrogen chloride, while cooled with ice, and then the solvent was distilled off. The resulting residue was dissolved in diethyl ether, and the solution was washed with water, dried over anhydrous magnesium sulfate, and distilled to give an oily substance having a boiling point of 108°-112° C./0.6 mmHg. Purification by column chromatography (silica gel-benzene) gave 1.1 g (50% yield) of ethyl 1-acetyl-2-(2,2,2-trichloroethyl)-3,3-dimethylcyclopropanecarboxylate.

Workup

  1. temperaturewas cooled with ice
  2. temperaturewhile cooled with ice
  3. distillationthe solvent was distilled off
  4. dissolutionThe resulting residue was dissolved in diethyl ether
  5. washthe solution was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationdistilled
  8. customto give an oily substance
  9. customPurification by column chromatography (silica gel-benzene)

Sources & evidence

ORD record
ord-1729d8718cbb477abfb95c1f594bc559
Source dataset
uspto-grants-1985_02
Patent number
US04500733

Reaction notes

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