Acetonitrile → 3-Acetoxycyclohexene

HRID 1834323Notes

Reaction equation

HRID 1834323 reaction equation
C(#N)C.[CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]=1.[C:10]([O:18]OC(C)(C)C)(=[O:17])[C:11]1C=CC=CC=1>[Cu].C(O)(=O)C>[C:10]([O:18][CH:4]1[CH2:9][CH2:8][CH2:7][CH:6]=[CH:5]1)(=[O:17])[CH3:11]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 8079CyclohexeneHCID 11966tert-Butyl peroxybenzoate

Product 1

HCID 111161483-Acetoxycyclohexene

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 1.100 g of the copper complex of N-salicylidene-3-amino-3-deoxy-1,2-O-isopropylidene-5-O-triphenylmethyl-α-D-ribofuranose, 0.70 g of copper powder, 15 ml of acetonitrile, 5 ml of acetic acid, 15 ml of cyclohexene and 5 of t-butyl peroxybenzoate was stirred at room temperature for 9 hours in a nitrogen atmosphere. After filtering the reaction solution, the filtrate was treated in the same manner as in Example 1 to obtain 1.80 g of 2-cyclohexenyl acetate.

Workup

  1. filtrationAfter filtering the reaction solution
  2. additionthe filtrate was treated in the same manner as in Example 1

Sources & evidence

ORD record
ord-afe8e3ceb2824bbf8d1847528e83e154
Source dataset
uspto-grants-1978_01
Patent number
US04069385

Reaction notes

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