Acetonitrile → 3-Acetoxycyclohexene

HRID 1834321Notes

Reaction equation

HRID 1834321 reaction equation
C(=N[C@H](C1C=CC=CC=1)C)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C1CCCCC=1.C(#N)C.[C:27](OOC(C)(C)C)(=[O:34])[C:28]1C=CC=CC=1>[Cu].C(O)(=O)C>[C:27]([O:4][CH:3]1[CH2:2][CH2:8][CH2:7][CH:6]=[CH:5]1)(=[O:34])[CH3:28]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 8079CyclohexeneHCID 11966tert-Butyl peroxybenzoateHCID 135405060(S)-(+)-N-salicylidene-1-phenylethylamine

Product 1

HCID 111161483-Acetoxycyclohexene

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 0.451 g of (S)-(+)-N-salicylidene-1-phenylethylamine, 0.182 g of cupric acetate, 0.7 g of copper powder, 15 ml of cyclohexene, 15 ml of acetonitrile, 5 ml of acetic acid and 5 ml of t-butyl peroxybenzoate was stirred at 20° to 25° C for 6.5 hours in a nitrogen atmosphere. After the reaction, the reaction mixture was treated in the same manner as in Example 1 to obtain 1.60 g of 2-cyclohexenyl acetate.

Workup

  1. customAfter the reaction
  2. additionthe reaction mixture was treated in the same manner as in Example 1

Sources & evidence

ORD record
ord-d1d2dbc790ea40f888fd8db2c8af8397
Source dataset
uspto-grants-1978_01
Patent number
US04069385

Reaction notes

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