m-Chloroperbenzoic acid → HCID 21553460, compound

HRID 268111Notes

Reaction equation

HRID 268111 reaction equation
[Cl:1][CH2:2][CH2:3][CH:4]1[CH:8](C(=O)C)[CH2:7][CH:6](C(=O)C)[CH:5]1[C:15]#[N:16].ClC1C=CC=[C:20]([C:24]([O:26]O)=[O:25])C=1>C(Cl)(Cl)Cl>[Cl:1][CH2:2][CH2:3][CH:4]1[CH:8]([O:26][C:24](=[O:25])[CH3:20])[CH2:7][CH:6]([O:26][C:24](=[O:25])[CH3:20])[CH:5]1[C:15]#[N:16]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21553457HCID 21553457, compound

Product 1

HCID 21553460HCID 21553460, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 0.46 g of 2-(2'-chloroethyl)-3,5-diacetyl-cyclopentanecarbonitrile, 2.05 g of meta-chloroperbenzoic acid and 15 ml of chloroform was heated at 50°C for 4 days. The reaction mixture was treated by the same procedure as set forth in Example 32 to afford 0.40 g of 2-(2'-chloroethyl)-3,5-diacetoxy-cyclopentanecarbonitrile as an oily substance. The product had the following characteristics: Infrared absorption (film method): 2250, 1740, 1430, 1370, 1230, 1045, 1020. Nuclear magnetic resonance (in CDCl3): about 5.3 (two multiplet, 2H, two methyne protons at the 3- and 5-position), 3.65 (triplet, J=7 cps, methylene protons adjacent to chlorine), 2.10 (two singlets, two acetoxy protons).

Workup

  1. additionThe reaction mixture was treated by the same procedure

Sources & evidence

ORD record
ord-eb50ca1221e74ef086ccaad8d3b36aeb
Source dataset
uspto-grants-1976_03
Patent number
US03946065

Reaction notes

Loading…