Cyclopentadiene → HCID 20345173, compound

HRID 2049496Notes

Reaction equation

HRID 2049496 reaction equation
B(F)(F)F.[CH3:5]COCC.[CH:10]1[CH2:14]C=[CH:12][CH:11]=1.[CH:15]([C:17]([CH3:21])=[CH:18][CH2:19][Cl:20])=[O:16].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[Cl:20][CH2:19][CH:18]1[C:17]([CH3:5])([CH:15]=[O:16])[CH:21]2[CH2:12][CH:11]1[CH:10]=[CH:14]2

Participants

6

Reactant 4

HCID 7612CyclopentadieneHCID 8000Boron trifluoride etherateHCID 10340Sodium CarbonateHCID 30141924-Chloro-2-methyl-2-butenal

Product 1

HCID 20345173HCID 20345173, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

5 ml of boron fluoride etherate were added to 1 liter of methylene chloride and the mixture was cooled to -20° C. A solution of 452 g (6.84 moles) of cyclopentadiene and 712 g (6.0 moles) of 3-formyl-crotyl chloride were added, whilst stirring, at a rate such that the reaction temperature did not rise above -10° C. The reaction mixture was then stirred for 3 hours at -10° C. To work up the reaction mixture, it was poured onto 1 kg of ice and neutralized with sodium carbonate solution, and the methylene chloride solution was washed neutral with water. After distilling off the solvent under reduced pressure (12 mm Hg/50° C.), 1,139 g of reaction product remained. A sample distillation showed that the yield was about 90% of theory.

Workup

  1. customdid not rise above -10° C
  2. stirringThe reaction mixture was then stirred for 3 hours at -10° C
  3. washthe methylene chloride solution was washed neutral with water
  4. distillationAfter distilling off the solvent
  5. customunder reduced pressure (12 mm Hg/50° C.), 1,139 g of reaction product
  6. distillationA sample distillation

Sources & evidence

ORD record
ord-2433d5771b5b432b96c3bc19d117ad80
Source dataset
uspto-grants-1980_04
Patent number
US04197411

Reaction notes

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