Organic synthesis with α-chloro sulphides. Preparation of aromatic γ-lactones from phenols and α-chloro sulphide carboxylates
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 4,p. 1041-1045
- https://doi.org/10.1039/p19900001041
Abstract
Lewis acid-catalysed alkylation of para-substituted phenols using α-chloro sulphides as electrophiles yields sulphenylated γ-lactones which can be desulphurised with zinc in acetic acid or Raney nickel. This synthesis has been applied to p-cresol, 2-naphthol, and two phenolic dihydrocinnamates. Alkylation of 1,4-dimethoxybenzene yields homogentisic acid dimethyl ether after desulphurisation and hydrolysis.Keywords
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