Hydrochloric Acid → Ethyl 4,6,6-trichloro-3,3-dimethyl-5-hexenoate

HRID 1762762Notes

Reaction equation

HRID 1762762 reaction equation
[O-]CC.[Na+].[Cl:5][CH:6]([CH2:16][C:17](Cl)([Cl:19])[Cl:18])[C:7]([CH3:15])([CH3:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].Cl>CN(C)C=O>[Cl:5][CH:6]([CH:16]=[C:17]([Cl:18])[Cl:19])[C:7]([CH3:15])([CH3:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 108412Hexanoic acid, 4,6,6,6-tetrachloro-3,3-dimethyl-, ethyl esterHCID 2723922Sodium ethoxide

Product 1

HCID 3042523Ethyl 4,6,6-trichloro-3,3-dimethyl-5-hexenoateYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2.04 g of sodium ethoxide in 60 ml of dimethylformamide was added to a hot solution (140°) of 3.1 g of ethyl 4,6,6,6-tetrachloro-3,3-dimethylhexanoate in 20 ml of dimethylformamide. The mixture was maintained at 140° for 2 hours, then cooled to 0°, neutralized with dry hydrogen chloride and poured into ice water. The aqueous mixture was extracted with ether, and the extract was washed successively with saturated aqueous sodium bicarbonate and sodium chloride. The washed extract was dried over magnesium sulfate and distilled to give 1.81 g (77% yield) of ethyl 4,6,6-trichloro-3,3-dimethyl-5-hexenoate, b.p. 98°-101°/0.6 mm.

Workup

  1. temperatureThe mixture was maintained at 140° for 2 hours
  2. temperaturecooled to 0°
  3. extractionThe aqueous mixture was extracted with ether
  4. washthe extract was washed successively with saturated aqueous sodium bicarbonate and sodium chloride
  5. extractionThe washed extract
  6. dry with materialwas dried over magnesium sulfate
  7. distillationdistilled

Sources & evidence

ORD record
ord-1a0a1589deeb4f5cad35e779c5d2bdd8
Source dataset
uspto-grants-1989_05
Patent number
US04833266

Reaction notes

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