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Organic Lab Reactions 164

Organic Lab Reactions 164 - 60-80° yields 5.92 g(89.5 of...

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GENERAL PROCEDURE 159 is allowed to stand at room temperature for about two hours. The reagent is then largely removed with a stream of air and the residue neutralized with sodium carbonate solution and extracted with benzene. This is washed with water, shaken with a little anhydrous sodium sul- fate, and concentrated to remove the benzene. The residual oil is dis- tilled under reduced pressure as in Procedure II, giving 6.2 g. (94%) of nearly colorless ketone. A single crystallization from ligroin (b.p.
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Unformatted text preview: 60-80°) yields 5.92 g. (89.5%) of pure ketone, m.p. 89.5-90.5°, remelt-ing 1846 at 96.5-97.5°. As much as 67 g. of 7-2-naphthylbutyric acid, using 500 g. of hydrogen fluoride, has been cyclized at one time. 186 The yield of pure~ketone was 94%. The method also is applicable to the cyclization of o-benzylbenzoic acids to anthrones. 129 1846 The double melting point corresponds to two polymorphic forms (reference 97). 186 Adkins and Lohr, unpublished observation...
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