Hydrogen Peroxide → Sec.Butyl Bis(beta-Carboxyethyl)Phosphine Oxide

HRID 485927Notes

Reaction equation

HRID 485927 reaction equation
C(P)(CC)C.C(OC)(=[O:9])C=C.N(C(C(C)C)C#N)=NC(C(C)C)C#N.[CH:26]([P:30]([CH2:37][CH2:38][C:39]([O:41]C)=[O:40])[CH2:31][CH2:32][C:33]([O:35]C)=[O:34])([CH2:28][CH3:29])[CH3:27].OO>>[CH:26]([P:30](=[O:9])([CH2:37][CH2:38][C:39]([OH:41])=[O:40])[CH2:31][CH2:32][C:33]([OH:35])=[O:34])([CH2:28][CH3:29])[CH3:27]

Participants

6

Reactant 5

HCID 784Hydrogen PeroxideHCID 7294Methyl AcrylateHCID 11240960Butanenitrile, 2,2'-azobis[3-methyl-HCID 13810228(Butan-2-yl)phosphaneHCID 131714320Sec. butylbis(carbomethoxyethyl)phosphine

Product 1

HCID 22902895Sec.Butyl Bis(beta-Carboxyethyl)Phosphine Oxide

Procedure

Sec. butylphosphine, 592 parts (85% purity) is reacted with 860 parts of methyl acrylate containing 4.9 parts of azobis(isovaleronitrile) at 67°-100° C. for 3.5 hours. The reaction product, sec. butylbis(carbomethoxyethyl)phosphine is reacted with 10% molar excess hydrogen peroxide (25% solution) for two hours at 60° C. to give the corresponding phosphine oxide. The latter is hydrolyzed with dilute sulfuric acid to give after recrystallization from water, sec. butyl bis(β-carboxyethyl)phosphine oxide.

Sources & evidence

ORD record
ord-79fe421a302d4e3aa58cc969247964e1
Source dataset
uspto-grants-1985_08
Patent number
US04537993

Reaction notes

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