4-Hydroxybenzaldehyde → HCID 243062, compound

HRID 358123Notes

Reaction equation

HRID 358123 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:11].C(O)(=O)C>C(O)C.C([O-])(=O)C.[NH4+]>[C:10]([C:12](=[CH:6][C:5]1[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:11]

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 176Acetic AcidHCID 7764Ethyl cyanoacetate

Product 1

HCID 243062HCID 243062, compoundYield 121.8%

Reagents, catalysts & solvents 2

HCID 517165Ammonium AcetateCatalystHCID 702EthanolSolvent

Procedure

30 g of 4-hydroxybenzaldehyde, 31.7 g of ethyl cyanoacetate, 4.5 ml of acetic acid and 1.9 g of ammonium acetate were refluxed in 100 ml of ethyl alcohol for 4 hours with heating. After the reaction, the reaction solution was poured into 500 ml of ice water to separate crystals. The resulting crystals were recrystallized from 400 ml of methyl alcohol to obtain 65 g of ethyl 2-cyano-3-(4-hydroxyphenyl)acrylate having a melting point of 89° to 91° C. 10.9 g of the resulting compound and 4.3 g of pyridine were dissolved in 100 ml of tetrahydrofuran, and 4.5 g of acryloyl chloride was added dropwise thereto. The reaction was carried out for 2 hours while maintaining the reaction temperature below 40° C. After the reaction, the reacting solution was poured into ice water to separate crystals, and the resulting crystals were recrystallized from 100 ml of methyl alcohol to obtain 11 g of the desired compound having a melting point of 82° to 85° C. The identification of the compound was carried out using IR spectrum, NMR spectrum and elemental analysis.

Workup

  1. temperaturewith heating
  2. customAfter the reaction
  3. customto separate crystals
  4. customThe resulting crystals were recrystallized from 400 ml of methyl alcohol

Sources & evidence

ORD record
ord-6235cdc293e343388ace723109b64a0f
Source dataset
uspto-grants-1984_08
Patent number
US04464463

Reaction notes

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