Ethyl cyanoacetate → HCID 54235006, compound

HRID 1579320Notes

Reaction equation

HRID 1579320 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([CH:12]=O)=[CH:6][C:5]=1[O:14][CH3:15].[CH2:17]([O:19][C:20](=[O:24])[CH2:21][C:22]#[N:23])[CH3:18]>N1CCCCC1>[CH2:17]([O:19][C:20](=[O:24])[C:21]([C:22]#[N:23])=[CH:12][C:7]1[CH:8]=[C:9]([O:10][CH3:11])[C:4]([C:3]([O:2][CH3:1])=[O:16])=[C:5]([O:14][CH3:15])[CH:6]=1)[CH3:18]

Participants

4

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 12668400Methyl 4-formyl-2,6-dimethoxybenzoate

Product 1

HCID 54235006HCID 54235006, compound

Reagents, catalysts & solvents 1

HCID 8082PiperidineCatalyst

Conditions

Temperature
120 °C

Procedure

A mixture of 11.2 g. of 2,6-dimethoxy-4-formyl-benzoic acid methyl ester, 6.3 g. of cyanoacetic acid ethyl ester and three drops of piperidine was heated in an open vessel with stirring to 120°C. and stirred at this temperature for an additional 15 minutes. The residue was recrystallized from ethyl acetate and yielded α-cyano-3,5-dimethoxy-4-methoxycarbonyl-cinnamic acid ethyl ester, having a m.p. of 142°-144°C.

Workup

  1. additionA mixture of 11.2 g
  2. stirringstirred at this temperature for an additional 15 minutes
  3. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5ff0de2fbf0046b886c48f2d2e8a638f
Source dataset
uspto-grants-1976_01
Patent number
US03931181

Reaction notes

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