Sodium ethoxide → Ethyl 6,6,6-trichloro-3,3-dimethyl-4-hexenoate

HRID 359172Notes

Reaction equation

HRID 359172 reaction equation
Br[CH:2]([CH2:12][C:13]([Cl:16])([Cl:15])[Cl:14])[C:3]([CH3:11])([CH3:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[O-]CC.[Na+]>O1CCCC1>[Cl:14][C:13]([Cl:15])([Cl:16])[CH:12]=[CH:2][C:3]([CH3:10])([CH3:11])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 12607835Ethyl 4-bromo-6,6,6-trichloro-3,3-dimethylhexanoate

Product 1

HCID 53438823Ethyl 6,6,6-trichloro-3,3-dimethyl-4-hexenoateYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Two milliliters of a solution of anhydrous tetrahydrofuran containing 709 mg (2 mmoles) of ethyl 4-bromo-6,6,6-trichloro-3,3-dimethylhexanoate was added dropwise to a suspension of 163 mg (2.4 mmoles) of sodium ethoxide in 20 ml of anhydrous tetrahydrofuran. The mixture was stirred at room temperature for about 16 hours, poured into ice water and extracted with diethyl ether. The extract was dried over magnesium sulfate and then distilled to give 448 mg (82% yield) of ethyl 6,6,6-trichloro-3,3-dimethyl-4-hexenoate, b.p. 83°-85°/0.1 mm.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe extract was dried over magnesium sulfate
  3. distillationdistilled

Sources & evidence

ORD record
ord-f122b52601e04442817bb2d69414c808
Source dataset
uspto-grants-1991_03
Patent number
US04999451

Reaction notes

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