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Organic Lab Reactions 130

Organic Lab Reactions 130 - and 7-2-naphthylbutyric apids...

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THE NAPHTHALENE NUCLEUS 125 in 96% yield from 7-m-methoxyphenylbutyric acid (IIII). Similar results were obtained with 7-m-tolylbutyric acid. 83 Occasionally a case may be found in which some of the isomeric ketone arising from ortho cyclization is formed, although in small proportion. For example, 2 ' CH 8 O CH 3 O Lin a small amount of 7-methoxyhydrindone-l (LVII, R >- CHs) accom- panied the main product LVI (R = CHs) in the cyclization of m- methoxyhydrocinnamic acid (LV, R = CH 3 ). The free hydroxy acid LV (R = H) was shown to respond similarly to cyclization giving the ketones LVI (R = H) and LVII (R = H) in«80 and 14% yields, respec- tively. 84 O (CH 2 )aCO 2 H LVI Lvn The Naphthalene Nucleus. The cyclization of jS-2-naphthylpropionic
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Unformatted text preview: and 7-2-naphthylbutyric apids generally leads to angular ring closure into the reactive 1-position of the nucleus. The resulting ketones there-fore have the basic structures LVIII and LIX, respectively. Examples may be found in Tables VI through XIII. Linear ring closure may be realized only under extraordinary circumstances (p. 123). The ring Evnt LIX closure of 7-l-naphthylbutyric acids nearly always results in the forma-tion of 1-ketotetrahydrophenanthrene (LX) derivatives which arise 83 Fieser and Dunn, J. Am. Chem. Soe., 58, 572 (1936). 84 Johnson and Anderson, unpublished observation....
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