Cyclohexanone → HCID 53895452, compound

HRID 1089359Notes

Reaction equation

HRID 1089359 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)=O.[C:13]1(=[O:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[OH-:20].[Na+]>CO>[CH3:10][O:9][C:7]([C:6]1[CH:11]=[CH:12][C:3]([CH:1]=[C:14]2[CH2:15][CH2:16][CH2:17][C:18](=[CH:1][C:3]3[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:20])=[CH:5][CH:4]=3)[C:13]2=[O:19])=[CH:4][CH:5]=1)=[O:8]

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 14798Sodium HydroxideHCID 15294Methyl 4-Formylbenzoate

Product 1

HCID 53895452HCID 53895452, compoundYield 289.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl p formylbenzoate (186.0 g, 1.13 mol) and cyclohexanone (50.4 g, 0.514 mol) in 1 L of methanol, prepared and maintained under an inert atmosphere in a 2 L, 3-necked, round bottom flask equipped with a mechanical stirrer, is added 20 mL of an aqueous solution containing sodium hydroxide (4.0 g, 0.1 mol). The mixture is stirred at ambient temperature for 4.5 hours and the reaction mixture is then filtered and the product dried to give 113.2 g of 2,6-bis(4'-methoxycarbonylbenzylidene)cyclohexanone. The filtrate is heated on a steam bath for 45 minutes, cooled and filtered to give an additional 27.9 g of product for a total yield of 141.1 g (70% of theory) of 2,6-bis(4'-methoxycarbonylbenzylidene)-cyclohexanone. The results from analyses of a sample recrystallized from acetic acid are:

Workup

  1. temperaturemaintained under an inert atmosphere in a 2 L
  2. custom3-necked, round bottom flask equipped with a mechanical stirrer
  3. filtrationthe reaction mixture is then filtered
  4. customthe product dried

Sources & evidence

ORD record
ord-17a417bd64f1403f98c55cfcf1f1ebe2
Source dataset
uspto-grants-1990_10
Patent number
US04965399

Reaction notes

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