Ethanol → 4-Tert-butyl-cyclohexyl 2-cyano-3,3-diphenylacrylate

HRID 2228358

Reaction equation

HRID 2228358 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:22]([CH:26]1[CH2:31]CC(O)[CH2:28][CH2:27]1)([CH3:25])([CH3:24])[CH3:23].C([O-])([O-])=O.[Na+].[Na+].C(O)C>CO>[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[CH2:28][CH2:27][CH:26]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:31][CH2:8]1)=[O:5])#[N:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 73914-tert-ButylcyclohexanolHCID 10340Sodium CarbonateHCID 243274Etocrylene

Product 1

HCID 184696124-Tert-butyl-cyclohexyl 2-cyano-3,3-diphenylacrylateYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

139 g (0.5 mol) of ethyl 2-cyano-3,3-diphenylacrylate (Uvinul 3035), 200 ml of 4-tert-butylcyclohexanol and 10 g of Na2CO3 were reacted together at 182° C. with distillative removal of the ethanol formed, assisted by a stream of nitrogen. After about 4 h, the reaction mixture was diluted with 300 ml of methanol and 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 130 g (67%) of 4-tert-butyl-cyclohexyl 2-cyano-3,3-diphenylacrylate as a colorless solid. [λmax 302 nm; E11 (MeOH) 324]

Workup

  1. customformed
  2. filtrationfiltered 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-45f3e225a61a469491743d307724e9f2
Source dataset
uspto-grants-2002_07
Patent number
US06416773B2

Linked notes

Loading…