Benzaldehyde → 1,4-Bis(phenylglyoxaloyl)benzene

HRID 1105974Notes

Reaction equation

[CH:1](=[O:10])[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C-]#N.[K+]>>[C:5]1([C:6](=[O:7])[C:6]([C:5]2[CH:8]=[CH:9][C:2]([C:1](=[O:10])[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:18])=[CH:3][CH:4]=2)=[O:7])[CH:8]=[CH:9][CH:2]=[CH:3][CH:4]=1

Participants

Reactant 3

HCID 240Benzaldehyde

HCID 9032Potassium Cyanide

HCID 12173Terephthalaldehyde

Product 1

HCID 1379051,4-Bis(phenylglyoxaloyl)benzene

Procedure

The benzoinic condensation of terephthalaldehyde (625 g) with benzaldehyde (2000 g) is effected in conditions strictly identical to those of example 1, while using 300 g of potassium cyanide, which represents 50% of the stoichiometrical proportion. The yield of pure bis-benzoin is 1516 g (94%). This product, when oxidized, yields 90% of very pure 1,4-bis (phenylglyoxyloyl) benzene. The tetraketone yield thus averages 85% with respect to the reacted terephthalic aldehyde.

Sources & evidence

ORD record: ord-8ac9f58f85ac4e93ac3fdd6eb45bcdd7
Source dataset: uspto-grants-1982_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04310699

Reaction notes

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