Benzaldehyde → Ethyl benzylidenecyanoacetate

HRID 1601479

Reaction equation

HRID 1601479 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10].O.[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Na+].[Na+].[Al+3].[Al+3].[Si+4].C([O-])([O-])=O.[K+].[K+]>>[C:9]([C:11](=[CH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10]

Participants

5

Reactant 4

HCID 240BenzaldehydeHCID 7764Ethyl cyanoacetateHCID 11430Potassium CarbonateHCID 72941443Sodium aluminosilicate

Product 1

HCID 74845Ethyl benzylidenecyanoacetateYield 98%

Conditions

Temperature
90 °C

Procedure

10.61 g of benzaldehyde (0.1 mol) and 11.31 g of ethyl cyanoacetate (0.1 mol) are placed in a flask equipped with a reflux condenser and heated to 90° C. 1.0 g of zeolite A (supplied by Merck: MS 3 Å) and 0.5 g of K2CO3 are then added in succession. The reaction starts immediately and is complete after about 4 minutes. The reaction mixture is filtered while still hot, giving ethyl cyanocinnamate in a purity of >96%. The yield is 98%.

Workup

  1. customequipped with a reflux condenser
  2. filtrationThe reaction mixture is filtered while still hot,

Sources & evidence

ORD record
ord-48599a4b195b4f949db63b55e7d7669b
Source dataset
uspto-grants-1999_11
Patent number
US05977290

Linked notes

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