Hydrochloric Acid → Ethyl 4,6,6-tribromo-3,3-dimethylhex-5-enoate

HRID 1762764Notes

Reaction equation

HRID 1762764 reaction equation
[Na].[Br:2][CH:3]([CH2:13][C:14](Br)([Br:16])[Br:15])[C:4]([CH3:12])([CH3:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].Cl>C(O)C>[Br:2][CH:3]([CH:13]=[C:14]([Br:15])[Br:16])[C:4]([CH3:12])([CH3:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 13255636Ethyl 4,6,6,6-tetrabromo-3,3-dimethylhexanoate

Product 1

HCID 13321424Ethyl 4,6,6-tribromo-3,3-dimethylhex-5-enoateYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Two milliliters of an ethanolc solution containing 92 mg (4 mmoles) of sodium was added dropwise to a cold solution of 1.95 g (4 mmoles) of ethyl 4,6,6,6-tetrabromo-3,3-dimethylhexanoate in 10 ml of absolute ethanol. The cooled mixture was stirred for 2 hours, then poured into chilled 1N hydrochloric acid. The acidic mixture was extracted with diethyl ether, and the extract was washed successively with saturated aqueous bicarbonate and sodium chloride. The washed extract was dried over magnesium sulfate and distilled to give 846 mg (52% yield) of ethyl 4,6,6-tribromo-3,3-dimethyl-5-hexenoate, b.p. 130°-133°/0.3 mm.

Workup

  1. additionpoured
  2. extractionThe acidic mixture was extracted with diethyl ether
  3. washthe extract was washed successively with saturated aqueous bicarbonate and sodium chloride
  4. extractionThe washed extract
  5. dry with materialwas dried over magnesium sulfate
  6. distillationdistilled

Sources & evidence

ORD record
ord-e4545ac86fe94ee4b5b9b2d572348573
Source dataset
uspto-grants-1989_05
Patent number
US04833266

Reaction notes

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