Synthesis of phthalides and related topics and the isomerisation of a homophthalic acid derivative

Allison, William R (1960) Synthesis of phthalides and related topics and the isomerisation of a homophthalic acid derivative. PhD thesis, University of Glasgow.

Abstract

(a) The scope of the photobromination technique as a synthetic route to phthalide derivatives is discussed. The yields by this route have been improved by a new method for hydrolysis of orthobromethyl esters to the corresponding bromophthalides. Thus ethyl dibromo-orsellinate has been converted into 5,7-dihydroxyphthalide, and ethyl everninate has been converted into 7-hydroxy-5-methoxyphthalide. The relatively weak nature of the intramolecular hydrogen bond in 7-hydroxyphthalides has been further confirmed. (b) A proposed synthesis of 7-methoxybenzo[1',2',5,6] phthalide using the above methods, required l-hydroxy-3-methyl-2-naphthoic acid as starting material. On repeating the literature method for preparation of the latter, a new compound was obtained, which has been identified as 2-carboxy-3-methyl-4-phenyl-3-butenoic acid. A mechanism has been proposed for its formation.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Additional Information: Adviser: G T Newbold
• Keywords: Organic chemistry
• Date of Award: 1960
• Depositing User: Enlighten Team
• Unique ID: glathesis:1960-73510
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 14 Jun 2019 08:56
• Last Modified: 14 Jun 2019 08:56
• URI: https://theses.gla.ac.uk/id/eprint/73510