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Hydrochloric Acid → Ethyl beta-(3,3-dichloroallyl)isovalerate (ethyl 6,6-dichloro-3,3-dimethyl-5-hexenoate)

HRID 647558
Notes
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Reaction equation

HRID 647558 reaction equation
[Na].[CH2:2]([CH:4]([C:8]([CH3:16])([CH3:15])[CH2:9][CH2:10][C:11](Cl)([Cl:13])[Cl:12])[C:5]([OH:7])=[O:6])[CH3:3].[Cl:17][C:18](Cl)([Cl:30])[CH2:19][CH2:20][C:21]([CH3:29])([CH3:28])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].Cl>C(O)C>[CH2:2]([CH:4]([C:8]([CH3:15])([CH3:16])[CH2:9][CH:10]=[C:11]([Cl:12])[Cl:13])[C:5]([OH:7])=[O:6])[CH3:3].[Cl:17][C:18]([Cl:30])=[CH:19][CH2:20][C:21]([CH3:29])([CH3:28])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 131713141Ethyl beta-(3,3,3-trichloropropyl)isovalerate(ethyl 6,6,6-trichloro-3,3-dimethylhexanoate)

Product 1

HCID 86739063Ethyl beta-(3,3-dichloroallyl)isovalerate (ethyl 6,6-dichloro-3,3-dimethyl-5-hexenoate)Yield 79%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent
2×

Procedure

In 50 g of ethanol were dissolved 2.5 g of sodium metal and 20.0 g of the above ethyl β-(3,3,3-trichloropropyl)isovalerate were added to the solution. The mixture was refluxed for 8 hours. The reaction mixture was neutralized with a solution of hydrogen chloride in dry ethanol and concentrated to about one-twentieth of its original volume. To this concentrate were added 100 g of ice-water and the mixture was extracted with diethyl ether. The ethereal layer was dried over anhydrous magnesium sulfate and distilled to remove the low-boiling fraction. By the above procedure there were obtained 13.7 g of ethyl β-(3,3-dichloroallyl)isovalerate (ethyl 6,6-dichloro-3,3-dimethyl-5-hexenoate), the NMR spectrum of which is given below (yield: 79%).

Workup

  1. additionwere added to the solution
  2. temperatureThe mixture was refluxed for 8 hours
  3. concentrationconcentrated to about one-twentieth of its original volume
  4. additionTo this concentrate were added 100 g of ice-water
  5. extractionthe mixture was extracted with diethyl ether
  6. dry with materialThe ethereal layer was dried over anhydrous magnesium sulfate
  7. distillationdistilled
  8. customto remove the low-boiling fraction

Sources & evidence

ORD record
ord-d2b7a82f162f4761a37570b6200f9dcf
Source dataset
uspto-grants-1983_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04409238

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes