Hydrogen Peroxide → HCID 22902905, compound
Reaction equation
C[O:2]C(=O)C=C.C(P)C(C)C.N(C(C)(C)C#N)=NC(C)(C)C#N.[CH2:24]([P:28]([CH2:35][CH2:36][C:37]([O:39]C)=[O:38])[CH2:29][CH2:30][C:31]([O:33]C)=[O:32])[CH:25]([CH3:27])[CH3:26].OO>C1(C)C=CC=CC=1>[CH2:24]([P:28](=[O:2])([CH2:35][CH2:36][C:37]([OH:39])=[O:38])[CH2:29][CH2:30][C:31]([OH:33])=[O:32])[CH:25]([CH3:27])[CH3:26]Participants
Procedure
A solution of 688 parts of methylacrylate in 285 parts of toluene is reacted with 450 parts of 80% isobutylphosphine in the presence of 3.9 parts of (azobisisobutyronitrile) initiator at 74°-93° C. for 7 hours. The resulting isobutylbis(carbomethoxyethyl)phosphine is oxidized with 600 parts of (10% excess) of 25% aqueous hydrogen peroxide. The reaction is complete within 2-3 hours at 65° C. and the resultant phosphine oxide is isolated as an oil following distillation of toluene and water from the mixture. The recovered phosphine oxide is hydrolyzed in 4 liters of 5% aqueous sulfuric acid solution by refluxing over a 7 hour period. On cooling, the product, isobutyl bis(β-carboxyethyl)phosphine oxide is isolated as a white crystalline solid in 70% yield and purified by recrystallization from water, m.p. 186°-187° C.
Sources & evidence
- ORD record
- ord-f56d2abdd65146cdb12db594e41d4430
- Source dataset
- uspto-grants-1985_08
- Patent number
- US04537993
Reaction notes
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