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

HRID 359175Notes

Reaction equation

HRID 359175 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 millileters of an ethanolic 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 sodium 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 sodium bicarbonate and sodium chloride
  4. extractionThe washed extract
  5. dry with materialwas dried over magnesium sulfate
  6. distillationdistilled

Sources & evidence

ORD record
ord-84d1509545414570bccc584eb8f86252
Source dataset
uspto-grants-1991_03
Patent number
US04999451

Reaction notes

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