Cyclopentadiene → HCID 20345174, compound

HRID 2049497Notes

Reaction equation

HRID 2049497 reaction equation
B(F)(F)F.[CH3:5]COCC.[CH:10]1[CH2:14]C=[CH:12][CH:11]=1.[C:15]([O:18][CH2:19][CH:20]=[C:21]([CH:23]=[O:24])[CH3:22])(=[O:17])[CH3:16].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:15]([O:18][CH2:19][CH:20]1[C:21]([CH3:5])([CH:23]=[O:24])[CH:22]2[CH2:12][CH:11]1[CH:10]=[CH:14]2)(=[O:17])[CH3:16]

Participants

6

Reactant 4

HCID 7612CyclopentadieneHCID 8000Boron trifluoride etherateHCID 846993-Formylbut-2-enyl acetateHCID 516892Sodium Bicarbonate

Product 1

HCID 20345174HCID 20345174, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

5 ml of boron fluoride etherate were added to 400 ml of methylene chloride and the mixture was cooled to -15° C. A solution of 132 g (2 moles) of freshly distilled cyclopentadiene and 256 g (1.8 moles) of 3-formylcrotyl acetate was added dropwise, whilst stirring, at a rate such that the reaction temperature did not rise above -10° C. The reaction was then allowed to continue for 2 hours at -10° C., whilst stirring. For working up, about 0.5 kg of ice was added, the mixture was neutralized with sodium bicarbonate solution, the aqueous phase was separated off and the methylene chloride was removed under reduced pressure (12 mm Hg/50° C.). The reaction product which remained was subjected to fractional distillation, giving 337 g of main fraction (yield: 90%).

Workup

  1. customdid not rise above -10° C
  2. stirringwhilst stirring
  3. customthe aqueous phase was separated off
  4. customthe methylene chloride was removed under reduced pressure (12 mm Hg/50° C.)
  5. distillationThe reaction product which remained was subjected to fractional distillation
  6. customgiving 337 g of main fraction (yield: 90%)

Sources & evidence

ORD record
ord-057fa6e1f5d941bdbd0f14bef9c6cca8
Source dataset
uspto-grants-1980_04
Patent number
US04197411

Reaction notes

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