Org. Synth. 1949, 29, 1
DOI: 10.15227/orgsyn.029.0001
1-ACETYLCYCLOHEXENE
[Ketone, 1-cyclohexenyl methyl]
Submitted by J. H. Saunders
1
Checked by E. L. Jenner and R. S. Schreiber.
1. Procedure
In a
500-ml. round-bottomed flask are placed
40 g. (0.32 mole) of 1-ethynylcyclohexanol (p. 416),
250 ml. of dry benzene,
10 g. of phosphorus pentoxide, and a boiling chip. A
reflux condenser is attached to the flask, and the
benzene solution is refluxed gently on a steam cone for 2.5 hours. At the end of that time the contents of the flask are cooled and the
benzene is decanted from the
phosphorus pentoxide, washed once with
100 ml. of 5% sodium bicarbonate solution, and dried over
15 g. of anhydrous sodium sulfate. The
benzene is removed by distillation at atmospheric pressure, and the
acetylcyclohexene is carefully fractionated at reduced pressure, through a
15-cm. helix-packed column. The yield of material boiling at
85–88°/22 mm.,
nD20 1.4892, is
22.5–28 g. (
56–70%).
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3. Discussion
1-Acetylcyclohexene has been prepared by treating
cyclohexene with
acetyl chloride and
aluminum chloride,
2,3,4,5 by treating
1-ethynylcyclohexanol with
oxalic acid6 or
85% aqueous formic acid,
5,7,8,9 and by the dehydrohalogenation and hydrolysis of
ethylidenecyclohexane nitrosochloride.
10 1-Acetylcyclohexene and its homologs also have been prepared by the addition of a suitable diene to
vinylacetylene in the presence of water and a
mercury salt.
11
Appendix
Chemical Abstracts Nomenclature (Collective Index Number);
(Registry Number)
ethylidenecyclohexane nitrosochloride
Benzene (71-43-2)
acetyl chloride (75-36-5)
sodium bicarbonate (144-55-8)
Cyclohexene (110-83-8)
sodium sulfate (7757-82-6)
formic acid (64-18-6)
Oxalic acid (144-62-7)
mercury (7439-97-6)
aluminum chloride (3495-54-3)
1-Acetylcyclohexene,
Ketone, 1-cyclohexenyl methyl,
acetylcyclohexene (932-66-1)
1-Ethynylcyclohexanol (78-27-3)
vinylacetylene (689-97-4)
phosphorus pentoxide (1314-56-3)
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