Acetonitrile → 3-Acetoxycyclohexene
Reaction equation
C(=N[C@H](C1C=CC=CC=1)CC1C=CC(C)=CC=1)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C1CCCCC=1.C(#N)C.[C:34](OOC(C)(C)C)(=[O:41])[C:35]1C=CC=CC=1>[Cu].C1C=CC=CC=1.C(O)(=O)C>[C:34]([O:4][CH:3]1[CH2:2][CH2:8][CH2:7][CH:6]=[CH:5]1)(=[O:41])[CH3:35]Participants
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 0.50 g of the copper complex of (S)-(-)-N-salicylidene-1-phenyl-2-(p-tolyl)ethylamine, 0.045 g of copper powder, 25 ml of cyclohexene, 25 ml of acetonitrile, 5 ml of acetic acid and 5 ml of t-butyl peroxybenzoate was heated with stirring at 70° C for 7 hours in a nitrogen atmosphere. After cooling, the reaction mixture was admixed with 50 ml of benzene, washed successively with a 2N aqueous hydrochloric acid solution, water, an aqueous solution saturated with sodium hydrogen carbonate and an aqueous solution saturated with sodium chloride, and dried over anhydrous sodium sulfate. After evaporating the solvent, the residue was distilled under reduced pressure to obtain 1.88 g of 2-cyclohexenyl acetate. B.P. 75°-76° C/21 mmHg.
Workup
- temperaturewas heated
- temperatureAfter cooling
- washwashed successively with a 2N aqueous hydrochloric acid solution, water
- dry with materialan aqueous solution saturated with sodium hydrogen carbonate and an aqueous solution saturated with sodium chloride, and dried over anhydrous sodium sulfate
- customAfter evaporating the solvent
- distillationthe residue was distilled under reduced pressure
Sources & evidence
- ORD record
- ord-62185435f3b64c9495415c3306017607
- Source dataset
- uspto-grants-1978_01
- Patent number
- US04069385
Reaction notes
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