Birch reduction of benzamide, m-methoxy-benzamide and terephthalic acid

<p>(1) In a variety of experimental procedures for Birch reduction at dry-ice temperature (-65 to -78°C), benzamide was reduced to 1,4-dihydrobenzamide: (a) By using Niem’s procedure (27), with lithium and ethanol in liquid ammonia at dry-ice temperature and where ethanol was added slowly after lithium addition, benzamide was reduced to 1,4-dihydrobenzamide., (b) By using Kuehne and Lambert’s method (20), with sodium and ethanol in liquid ammonia at dry-ice temperature, benzamide was reduced to 1,4-dihydrobenzamide., (c) Using Kuehne and Lambert’s method (20), with sodium and ethanol in liquid ammonia at -33°C (the boiling point of NH₃), benzamide was reduced to a new compound (possibly 3-cyclohexene-carboxamide) not fully characterized.</p><p>(2) m-Methoxybenzaminde when subjected to Birch reduction at -78°C or -33°C and with a 3.3 or 8 equivalents of sodium and ethanol by Kuehne and Lambert’s procedure (20), gave the following results: (a) With 3.3 equivalents of sodium and ethanol in liquid ammonia at -78°C, m-methoxybenzamide was reduced to 1,4-dihydro-3-methoxybenzamide.; (b) A reduction similar to (a) with added iron (1 p.p.m.), was done with no noticeably large effects.; (c) Birch reduction of m-methoxybenzamide at -33°C (the boiling point of ammonia), gave a new compound, not identified.; (d) m-Methoxybenzamide, with excess sodium (8 equivalent) at dry-ice temperature, was reduced to a light brownish liquid, not characterized.</p><p>(3) Terephthalic acid on Birch reduction with lithium and ethanol in liquid ammonia was reduced to a mixture of cis- and trans- 1,4-dihydroterephthalic acid. Cis- and trans- isomers were separated on the basis of difference in solubility, as cis-isomer is more soluble in cold water than trans-isomer.</p>

Name thesis:degree_name

Master of Science (M.S.)

Level thesis:degree_level

Thesis

Discipline thesis:degree_discipline

Graduate School

Year dc:date.available

1965

Author dc:creator

• Qazi, Abdul Hamid

Contributors dc:contributor

• Charles A. Matuszak

• Reduction (Chemistry)
• Physical Sciences and Mathematics

Licence

• http://rightsstatements.org/vocab/NKC/1.0/

Repository record dc:identifier

https://scholarlycommons.pacific.edu/uop_etds/1589

OAI identifier oai:identifier

oai:scholarlycommons.pacific.edu:uop_etds-2588