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

HRID 1263028Notes

Reaction equation

HRID 1263028 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 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 1 N 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-4a2656d1e38e4d1e8125f16f99af11c0
Source dataset
uspto-grants-1984_06
Patent number
US04454343

Reaction notes

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