Acetic Acid → 2-Ethylhexyl 3,5-di-tertiary-butyl-4-hydroxybenzylidenecyanoacetate

HRID 1584690Notes

Reaction equation

HRID 1584690 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[C:18]([CH2:20][C:21]([O:23][CH2:24][CH:25]([CH2:30][CH3:31])[CH2:26][CH2:27][CH2:28][CH3:29])=[O:22])#[N:19].N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1>[C:14]([C:11]1[CH:10]=[C:7]([CH:6]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[C:12]=1[OH:13])[CH:8]=[C:20]([C:18]#[N:19])[C:21]([O:23][CH2:24][CH:25]([CH2:30][CH3:31])[CH2:26][CH2:27][CH2:28][CH3:29])=[O:22])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 963592-Ethylhexyl cyanoacetate

Product 1

HCID 542081222-Ethylhexyl 3,5-di-tertiary-butyl-4-hydroxybenzylidenecyanoacetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

28.1 g of 3,5-di-tertiary-butyl-4-hydroxybenzaldehyde were dissolved in 60 ml of toluene. 21.7 g of 2-ethylhexyl cyanoacetate, 0.27 g of piperidine and 0.67 g of acetic acid were added. The mixture was heated to reflux, and about 2 g of water were removed azeotropically. The clear solution was washed, dried and concentrated.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customabout 2 g of water were removed azeotropically
  4. washThe clear solution was washed
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8ac22db978ff4bd9aa906778166725b5
Source dataset
uspto-grants-1999_08
Patent number
US05935563

Reaction notes

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