3-Butenenitrile, 2-(acetyloxy)- → Isopentyl (3-acetoxy-3-cyanopropyl)methylphosphinate

HRID 745457Notes

Reaction equation

HRID 745457 reaction equation
[CH3:1][P:2]([O-:9])[O:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].[CH3:10][C:11]([O:13][CH:14]([C:17]#[N:18])[CH:15]=[CH2:16])=[O:12]>>[C:11]([O:13][CH:14]([C:17]#[N:18])[CH2:15][CH2:16][P:2]([CH3:1])(=[O:9])[O:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7])(=[O:12])[CH3:10]

Participants

3

Reactant 2

HCID 858913-Butenenitrile, 2-(acetyloxy)-HCID 131714779Isopentyl methanephosphonite

Product 1

HCID 54245807Isopentyl (3-acetoxy-3-cyanopropyl)methylphosphinateYield 102.3%

Conditions

Temperature
72 °C

Procedure

235.0 g of isopentyl methanephosphonite are heated to 72° C. under nitrogen. 0.5 g of tert.-amyl perpivalate is added to the solution, and 63.9 g of acrolein cyanohydrin acetate, in which 3.6 g of tert.-butyl pereodecanoate are dissolved, are added dropwise, with vigorous stirring at 72° C., within 2.75 hours. After reaction is complete, the mixture is stirred at 72° C. for 5 min, and 154.8 g of isopentyl methanephosphonite are distilled out. (Recovery: 94.8%). 143.8 g of 93.6% pure isopentyl (3-acetoxy-3-cyanopropyl)methylphosphinate (yield=97.9%) are obtained.

Workup

  1. dissolutionare dissolved
  2. additionare added dropwise
  3. customAfter reaction
  4. stirringthe mixture is stirred at 72° C. for 5 min
  5. distillation154.8 g of isopentyl methanephosphonite are distilled out

Sources & evidence

ORD record
ord-0875c69e944148a284e95bf7bdea6adb
Source dataset
uspto-grants-1986_07
Patent number
US04599207

Reaction notes

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