Acetic Acid → Methyl (E)-2-Cyano-3-phenylacrylate

HRID 1285511Notes

Reaction equation

HRID 1285511 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[N:2].[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(O)(=O)C.O>C1C=CC=CC=1.NCCC(O)=O>[C:1](/[C:3](=[CH:8]\[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)/[C:4]([O:6][CH3:7])=[O:5])#[N:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 962WaterHCID 7747Methyl cyanoacetate

Product 1

HCID 674252Methyl (E)-2-Cyano-3-phenylacrylateYield 91.3%

Reagents, catalysts & solvents 2

HCID 239Beta-AlanineCatalystHCID 241BenzeneSolvent

Procedure

A mixture containing 2.0 mL (22.7 mmoles) of methyl cyanoacetate, 2.38 g (22.4 mmoles) of benzaldehyde, 18 mg of β-alanine, and 1.00 mL of glacial acetic acid in 35 mL of benzene was heated at reflux for 2 hours with continuous azeotropic removal of water by means of a Dean-Stark trap. The product was isolated as described in the procedure of Example I, affording 3.83 g (91% yield) of crystalline cyanoester 2: mp 90°-91° C.

Workup

  1. temperaturewas heated
  2. customThe product was isolated

Sources & evidence

ORD record
ord-a0a0045e0c984678bffd59653a2e2e1a
Source dataset
uspto-grants-1986_01
Patent number
US04567265

Reaction notes

Loading…