(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.
(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.
(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.
","abstract_html":"<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 NH<sub>3</sub>), 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>","abstract_has_math":false,"creators":["Qazi, Abdul Hamid"],"institution":null,"degree_name":"Master of Science (M.S.)","degree_level":"Thesis","degree_discipline":"Graduate School","degree_department":null,"school":null,"contributors":["Charles A. Matuszak"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":1965,"date_issued":"1965-01-01T08:00:00Z","date_published":"1965-01-01T08:00:00Z","updated_at":"2026-07-24T05:37:34Z","subjects":["Reduction (Chemistry)","Physical Sciences and Mathematics"],"languages":[],"rights":[],"rights_urls":["http://rightsstatements.org/vocab/NKC/1.0/"],"identifier_entries":[]},"links":{"outbound_url":"https://scholarlycommons.pacific.edu/uop_etds/1589","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Charles A. Matuszak"]},{"key":"dc:creator","label":"Author","values":["Qazi, Abdul Hamid"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.available","label":"Dc Date Available","values":["2018-06-29T09:00:56Z"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Graduate School"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Thesis"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Master of Science (M.S.)"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Reduction (Chemistry)","Physical Sciences and Mathematics"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:rights","label":"Dc Rights","values":["http://rightsstatements.org/vocab/NKC/1.0/"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://scholarlycommons.pacific.edu/uop_etds/1589"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["(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.
(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.
(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.
"]},{"key":"dc:source","label":"Dc Source","values":["52"]},{"key":"dc:title","label":"Title","values":["Birch reduction of benzamide, m-methoxy-benzamide and terephthalic acid"]}]}],"canonical_facts":{"dc:contributor":["Charles A. Matuszak"],"dc:creator":["Qazi, Abdul Hamid"],"dc:date.available":["2018-06-29T09:00:56Z"],"dc:description.abstract":["(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.
(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.
(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.
"],"dc:identifier":["https://scholarlycommons.pacific.edu/uop_etds/1589"],"dc:rights":["http://rightsstatements.org/vocab/NKC/1.0/"],"dc:source":["52"],"dc:subject":["Reduction (Chemistry)","Physical Sciences and Mathematics"],"dc:title":["Birch reduction of benzamide, m-methoxy-benzamide and terephthalic acid"],"thesis:degree_discipline":["Graduate School"],"thesis:degree_level":["Thesis"],"thesis:degree_name":["Master of Science (M.S.)"]},"updated_at":"2026-07-24T05:37:34Z"}