Cyclopentanol → Cyclopentyl 2-cyano-3,3-diphenylacrylate

HRID 2228356

Reaction equation

HRID 2228356 reaction equation
[C:1]([C:3](=[C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].C([O-])([O-])=O.[Na+].[Na+].[CH:28]1(O)[CH2:32]CC[CH2:29]1>>[C:1]([C:3](=[C:9]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]([O:6][CH:7]1[CH2:32][CH2:28][CH2:29][CH2:8]1)=[O:5])#[N:2]

Participants

4

Reactant 3

HCID 7298CyclopentanolHCID 10340Sodium CarbonateHCID 243274Etocrylene

Product 1

HCID 18469614Cyclopentyl 2-cyano-3,3-diphenylacrylateYield 82%

Procedure

83.1 g (0.3 mol) of ethyl 2-cyano-3,3-diphenylacrylate (Uvinul 3035), 100 ml of cyclopentanol and 6 g of Na2CO3 were reacted with one another at 145° C. with distillative removal of the ethanol formed, assisted by a stream of nitrogen. After about 3 h, the reaction mixture was filtered hot in order to remove the Na2CO3. After the filtrate had been cooled, the precipitate which had formed was filtered off, washed with petroleum ether and dried, giving 78.1 g (82%) of cyclopentyl 2-cyano-3,3-diphenylacrylate as a colorless solid. [λmax 300 nm; E11 (MeOH) 395]

Workup

  1. customwith distillative removal of the ethanol
  2. customformed
  3. filtrationthe reaction mixture was filtered hot in order
  4. customto remove the Na2CO3
  5. temperatureAfter the filtrate had been cooled
  6. customthe precipitate which had formed
  7. filtrationwas filtered off
  8. washwashed with petroleum ether
  9. customdried

Sources & evidence

ORD record
ord-b39c8798215d43d9918b4720ad9af84d
Source dataset
uspto-grants-2002_07
Patent number
US06416773B2

Linked notes

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