Glyoxal → 1,2-Dihydroxy-1,2-bis(diphenylphosphinyl)ethane

HRID 65310Notes

Reaction equation

[CH:1]([CH:3]=[O:4])=[O:2].[C:5]1([PH:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C1C=CC=CC=1>[OH:2][CH:1]([P:11]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:18])[CH:3]([OH:4])[P:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:18]

Participants

Conditions

Temperature: 40 °C

Procedure

7.73 g of 30% aqueous glyoxal solution (40 mmols glyoxal), 16.17 g (80 mmols) of diphenylphosphine oxide and 40 ml of benzene were introduced into a round bottom flask. The initial pH of the reaction mixture was heated for 30 min with a water bath at 40° C. The precipitated white product was separated by filtration and weighed 16.64 g (90% yield) m.p. 211°-214° C. After recrystallization from dimethylsulfoxide-acetonitrile 3:2, V:V gave a sample of 1,2-dihydroxy-1,2-bis(diphenylphosphinyl)ethane m.p. 216°-217° C. Anal. Calcd for C26H24O4P2 : C, 67.53; H, 5.23. Found: C, 67.42; H, 5.34.

Workup

customThe precipitated white product was separated by filtration
customAfter recrystallization from dimethylsulfoxide-acetonitrile 3:2, V

Sources & evidence

ORD record: ord-c52dbab8ab0741118b98273825ecb68e
Source dataset: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04613674

Reaction notes

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