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

HRID 745455Notes

Reaction equation

HRID 745455 reaction equation
[CH3:1][P:2]([O-:9])[O:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[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][CH2:6][CH2:7][CH3:8])(=[O:12])[CH3:10]

Participants

3

Reactant 2

HCID 858913-Butenenitrile, 2-(acetyloxy)-HCID 131714778n-Pentyl methanephosphonite

Product 1

HCID 53637752n-Pentyl (3-acetoxy-3-cyanopropyl)methylphosphinateYield 101.1%

Procedure

242.0 g of n-pentyl methanephosphonite are heated to 80° C. under nitrogen, and 0.5 g of tert.-butyl perpivalate is added. 63.9 g of acrolein cyanohydrin acetate mixed with 2.5 g of tert.-butyl perpivalate are added dropwise to this solution within 2.25 hours. After reaction is complete, the mixture is stirred for 5 minutes, and 161.5 g of n-pentyl methanephosphonite are distilled out. (Purity: 91.2%, recovery: 93.4%). 142.1 g of n-pentyl (3-acetoxy-3-cyanopropyl)methylphosphinate (purity 94%; yield 97%) remain.

Workup

  1. addition0.5 g of tert.-butyl perpivalate is added
  2. additionare added dropwise to this solution within 2.25 hours
  3. customAfter reaction
  4. distillation161.5 g of n-pentyl methanephosphonite are distilled out

Sources & evidence

ORD record
ord-4b550c9c938748bd86726c3ab044f4d6
Source dataset
uspto-grants-1986_07
Patent number
US04599207

Reaction notes

Loading…