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

HRID 2119089Notes

Reaction equation

HRID 2119089 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-7591fc1c9f444feda856bff69131bfb6
Source dataset
uspto-grants-1987_07
Patent number
US04681953

Reaction notes

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