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

HRID 359173Notes

Reaction equation

HRID 359173 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-0f065f36bc1c4d42bb7d6ba809e303d1
Source dataset
uspto-grants-1991_03
Patent number
US04999451

Reaction notes

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