Hydrochloric Acid → Ethyl 6,6,6-trichloro-2,3,3-trimethylhex-4-enoate

HRID 359176Notes

Reaction equation

HRID 359176 reaction equation
Br[CH:2]([CH2:13][C:14]([Cl:17])([Cl:16])[Cl:15])[C:3]([CH3:12])([CH3:11])[CH:4]([CH3:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[O-]CC.[Na+].Cl>O1CCCC1>[Cl:15][C:14]([Cl:16])([Cl:17])[CH:13]=[CH:2][C:3]([CH3:12])([CH3:11])[CH:4]([CH3:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 12810690HCID 12810690, compound

Product 1

HCID 54466645Ethyl 6,6,6-trichloro-2,3,3-trimethylhex-4-enoateYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 737 mg of ethyl 4-bromo-6,6,6-trichloro-2,3,3-trimethylhexanoate in 20 ml of anhydrous tetrahydrofuran was cooled to 0°. To the cold solution was added 163 mg of sodium ethoxide and the mixture was stirred for 5 hours. The cooled mixture was poured into cold 1N hydrochloric acid and extracted with diethyl ether. The ether extract was washed successively with water, saturated aqueous sodium bicarbonate and aqueous sodium chloride, then dried over magnesium sulfate. The dried ether extract was distilled to give 430 mg (75% yield) of ethyl 6,6,6-trichloro-2,3,3-trimethyl-4-hexenoate, b.p. 92°-95°/0.2 mm.

Workup

  1. extractionextracted with diethyl ether
  2. extractionThe ether extract
  3. washwas washed successively with water, saturated aqueous sodium bicarbonate and aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. extractionThe dried ether extract
  6. distillationwas distilled

Sources & evidence

ORD record
ord-f6057dd1b7a941458cd57dc50307ee6b
Source dataset
uspto-grants-1991_03
Patent number
US04999451

Reaction notes

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