Long-chain phenols. Part 16. A novel synthesis of homologous orsellinic acids and their methyl ethers
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 8,p. 1658-1666
- https://doi.org/10.1039/p19800001658
Abstract
By the novel reaction of 3,5-dimethoxyfluorobenzene with n-alkyl-lithium compounds, followed by carbonation, homologous orsellinic acid dimethyl ethers (6-alkyl-2,4-dimethoxybenzoic acids) have been obtained. The reactions proceeded best with the homologues of methyl-lithium. These reactions are considered to occur by way of 3,5-dimethoxybenzyne. 2,4-Dimethoxyfluorobenzene did not form an aryne but gave 3-fluoro-2,6-dimethoxybenzoic acid instead. Decomposition with water of alkyl-lithium reaction mixtures from 3,5-dimethoxyfluorobenzene yielded 5-n-alkylresorcinol dimethyl ethers. Demethylation of 6-alkyl-2,4-dimethoxybenzoic acids with boron trichloride proceeded partially and selectively to give the 6-alkyl-2-hydroxy-4-methoxybenzoic acids, and completely with aluminium chloride to give the homologous orsellinic acids. Boron tribromide was less effective, but readily gave the 5-alkyl resorcinols from the corresponding dimethyl ethers.This publication has 1 reference indexed in Scilit:
- Long chain phenols. Part 15. Synthesis of 6-n-alkylsalicylic acids (and isomeric acids) from fluoroanisoles with alkyl-lithiumJournal of the Chemical Society, Perkin Transactions 1, 1979