Heptane → HCID 86739665, compound

HRID 2418802Notes

Reaction equation

HRID 2418802 reaction equation
[OH-].[K+].[Cl:3][C:4]([C:14]([F:17])([F:16])[F:15])=[CH:5][C@@H:6]1[C@H:8]([C:9]([OH:11])=[O:10])[C:7]1([CH3:13])[CH3:12].CCCCCCC.Cl[CH2:26][C:27]1[C:28]([CH3:39])=[C:29]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:30]=[CH:31][CH:32]=1>O.C(Cl)Cl.CCCCCC.C(OCC)C.C(#N)C>[Cl:3][C:4]([C:14]([F:15])([F:16])[F:17])=[CH:5][C@@H:6]1[C@H:8]([C:9]([O:11][CH2:26][C:27]2[C:28]([CH3:39])=[C:29]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:30]=[CH:31][CH:32]=2)=[O:10])[C:7]1([CH3:13])[CH3:12]

Participants

10

Reactant 4

HCID 8900HeptaneHCID 14797Potassium HydroxideHCID 132825193-(Chloromethyl)-2-methyl-1,1'-biphenylHCID 54318404cis-3-(2-Chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylic acid

Product 1

HCID 86739665HCID 86739665, compoundYield 54.8%

Reagents, catalysts & solvents 5

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of 0.62 g (0.011 mole) of potassium hydroxide in 3.65 ml distilled water was added, with stirring, 1.8 g (0.0074 mole) of cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylic acid and 14.6 ml of heptane. The reaction mixture was heated at reflux temperature, and the water was collected in a Dean-Stark trap. The anhydrous reaction mixture was then cooled, and 1.5 g (0.0069 mole) of 3-chloromethyl-2-methyl-[1,1'-biphenyl] and 14.6 ml of acetonitrile were added. The reaction mixture was stirred and heated at reflux temperature for 16 hours, then cooled and diluted with water. Diethyl ether was added and the two phases were separated. The aqueous phase was washed with heptane, then with diethyl ether. The organic phase and washings were combined, dried with anhydrous sodium sulfate and filtered. The solvents were removed from the filtrate under reduced pressure to give a yellow oil which was dissolved in methylene chloride and subjected to preparative liquid chromatography. A mixture of hexane and methylene chloride (2:1) was used as eluant. Appropriate fractions, as determined by thin layer and gas liquid phase chromatography, were combined to give 1.6 g of [2-methyl(1,1'-biphenyl)-3-yl]methyl cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate as a clear, colorless oil.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux temperature
  4. customthe water was collected in a Dean-Stark trap
  5. temperatureThe anhydrous reaction mixture was then cooled
  6. stirringThe reaction mixture was stirred
  7. temperatureheated
  8. temperatureat reflux temperature for 16 hours
  9. temperaturecooled
  10. customthe two phases were separated
  11. washThe aqueous phase was washed with heptane
  12. dry with materialdried with anhydrous sodium sulfate
  13. filtrationfiltered
  14. customThe solvents were removed from the filtrate under reduced pressure
  15. customto give a yellow oil which

Sources & evidence

ORD record
ord-ed31602a3f9e4c52a08ab77cfaa4bb73
Source dataset
uspto-grants-1984_09
Patent number
US04473709

Reaction notes

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