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1972•Journal of the Chemical Society Chemical CommunicationsRequires access

A new method of synthesis of aromatic dithioesters: participation of carbon disulphide in Friedel–Crafts reaction

Sukuru Raghu Ramadas, P. Srinivasan

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Abstract

Aralkyl ethers such as anisole reacted with γ-butyrolactone in carbon disulphide under Friedel–Crafts conditions affording the known methyl 4-methoxy-dithiobenzoate (I), in 28% yield and also the hitherto unknown ω-methoxycarbonylpropyl 4-methoxydithiobenzoate (II) in 54% yield after methylation and esterification of the initial reaction product, while benzene and toluene under similar conditions gave only the normal Friedel–Crafts products.

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What this paper is about

Aralkyl ethers such as anisole reacted with γ-butyrolactone in carbon disulphide under Friedel–Crafts conditions affording the known methyl 4-methoxy-dithiobenzoate (I), in 28% yield and also the hitherto unknown ω-methoxycarbonylpropyl 4-methoxydithiobenzoate (II) in 54% yield after methylation and esterification of the initial reaction product, while benzene and toluene under similar conditions gave only the normal Friedel–Crafts products.

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Available abstract

Aralkyl ethers such as anisole reacted with γ-butyrolactone in carbon disulphide under Friedel–Crafts conditions affording the known methyl 4-methoxy-dithiobenzoate (I), in 28% yield and also the hitherto unknown ω-methoxycarbonylpropyl 4-methoxydithiobenzoate (II) in 54% yield after methylation and esterification of the initial reaction product, while benzene and toluene under similar conditions gave only the normal Friedel–Crafts products.

Key concepts: Anisole, Friedel–Crafts reaction, Chemistry, Yield (engineering), Benzene, Toluene, Organic chemistry, Carbon fibers

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