Methylcyclopentadiene synthesis

Details Methylcyclopentadiene synthesis Methylcyclopentadiene synthesis

1982-04-23

1985-10-15

Shine, W. J.

Chemistry of hydrocarbon compounds

Alicyclic compound synthesis

By alkylation or alkyl transfer

585317, 585376, C07C 540

Patent

active

045476039

ABSTRACT:
Synthesis of methylcyclopentadiene with limited amounts of dimethylcyclopentadiene by-product. Cyclopentadiene monomer is complexed with metallic sodium in diglyme (diethylene glycol dimethylether) and reacted with an alkylating agent such as methyl chloride in the presence of a large stoichiometric excess of cyclopentadiene monomer. A high yield of methylcyclopentadiene is obtained with only a small production of undesirable methylcyclopentadiene. The excess cyclopentadiene is easily recycled in a continuous process.

REFERENCES:
patent: 2916504 (1959-12-01), Shapiro
patent: 2964547 (1960-12-01), De Witt et al.
McLean et al., Can. J. Chem., 41, 1231, (1963) (I).
Mironov et al., Tetrahedron, 19, 1939, (1963).
McLean et al., Tetrahedron, 21, 2313, (1965) (II).

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