Vanillin → 1-(p-Carboxyphenyl)-3-methyl-4-(3'-methoxy-4'-hydroxybenzylidene)-2-pyrazolin-5-one

HRID 1106099Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[CH2:13][C:12]([CH3:16])=[N:11]2)=[CH:6][CH:5]=1)([OH:3])=[O:2].O=[CH:18][C:19]1[CH:27]=[CH:26][C:24]([OH:25])=[C:21]([O:22][CH3:23])[CH:20]=1>CN(C)C=O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:14](=[O:15])[C:13](=[CH:18][C:19]3[CH:27]=[CH:26][C:24]([OH:25])=[C:21]([O:22][CH3:23])[CH:20]=3)[C:12]([CH3:16])=[N:11]2)=[CH:8][CH:9]=1)([OH:3])=[O:2]

Participants

Conditions

Temperature: 100 °C

Procedure

218 g (1 mole) of 1-p-carboxyphenyl-3-methyl-2-pyrazolin-5-one and 152 g (1 mole) of vanillin were dissolved in 500 ml of dimethylformamide. The reaction mixture was heated for 3 h at 100° C. After cooling down to room temperature the crystallized dye was filtered with suction and rinsed with methanol.

Workup

temperatureAfter cooling down to room temperature the crystallized dye
filtrationwas filtered with suction
washrinsed with methanol

Sources & evidence

ORD record: ord-1db8eb48ab9a43fbb50779ddf04ee0e5
Source dataset: uspto-grants-1982_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04311787

Reaction notes

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