Acetic Acid → alpha-Cyanocinnamic acid ethyl ester
Reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O)(=O)C.[OH-].[Na+]>C1C=CC=CC=1.NCCC(O)=O.O>[C:1](/[C:3](=[CH:9]\[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]Participants
Procedure
A mixture containing 4.0 mL (37.6 mmoles) of ethyl cyanoacetate, 3.95 g (37.2 mmoles) of benzaldehyde, 20 mg of β-alanine, and 1.00 mL of glacial acetic acid in 35 mL of benzene was heated at reflux for 3 hours with continuous azeotropic removal of water by means of a Dean-Stark trap. The product was isolated by cooling the mixture to room temperature, pouring it into 75 mL of 2:1 (v/v)1M aqueous NaOH:saturated brine, and extraction with ether. The organic extracts were washed with 75 mL of 2:1 (v/v) 1M aqueous NaOH:saturated brine, 10% aqueous sodium chloride solution, then were dried over anhydrous magnesium sulfate and subsequently filtered. Removal of the ether and benzene by evaporation at reduced pressure afforded 6.88 g (92% yield) of crystalline cyanoester 1: mp 49°-50° C.
Workup
- temperaturewas heated
- customThe product was isolated
- extractionsaturated brine, and extraction with ether
- washThe organic extracts were washed with 75 mL of 2:1 (v/v) 1M aqueous NaOH
- dry with materialsaturated brine, 10% aqueous sodium chloride solution, then were dried over anhydrous magnesium sulfate
- filtrationsubsequently filtered
- customRemoval of the ether and benzene
- customby evaporation at reduced pressure
Sources & evidence
- ORD record
- ord-2a3c5b4d1dd9420baa9cf6cee59fb2b5
- Source dataset
- uspto-grants-1986_01
- Patent number
- US04567265
Reaction notes
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