Cyclohexanol → Cyclohexyl 2-cyano-3,3-diphenylacrylate

HRID 2228357

Reaction equation

HRID 2228357 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].[CH:22]1(O)[CH2:27]CC[CH2:24][CH2:23]1.C([O-])([O-])=O.[Na+].[Na+]>C(O)C>[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[CH2:24][CH2:23][CH2:22][CH2:27][CH2:8]1)=[O:5])#[N:2]

Participants

5

Reactant 3

HCID 7966CyclohexanolHCID 10340Sodium CarbonateHCID 243274Etocrylene

Product 1

HCID 18469613Cyclohexyl 2-cyano-3,3-diphenylacrylateYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

139 g (0.5 mol) of ethyl 2-cyano-3,3-diphenylacrylate (Uvinul 3035), 200 ml of cyclohexanol and 10 g of Na2CO3 were reacted together at 150° C. with distillative removal of the ethanol formed, assisted by a stream of nitrogen. After about 6 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 111 g (67%) of cyclohexyl 2-cyano-3,3-diphenylacrylate as a colorless solid. [λmax 300 nm; E11, (MeOH) 381]

Workup

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

Sources & evidence

ORD record
ord-ad6ffa1e4b0242799ee1ca8e9eba4689
Source dataset
uspto-grants-2002_07
Patent number
US06416773B2

Linked notes

Loading…