4-Hydroxybenzaldehyde → HCID 243062, compound

HRID 1388490Notes

Reaction equation

HRID 1388490 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+]>[CH2:16]([O:15][C:13](=[O:14])[C:12]([C:10]#[N:11])=[CH:6][C:5]1[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=1)[CH3:17]

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

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

Workup

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

Sources & evidence

ORD record
ord-c58e31404a384a3389adc9a25a9f2b67
Source dataset
uspto-grants-1984_02
Patent number
US04431726

Reaction notes

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