Synthesis and Reactivity of 2‐Aroylbenzoic Acids, III. 2‐(4‐hydroxy‐3,5‐dimethylbenzoyl)benzoic Acid | Zendy

Rumiński Jan K. | Zendy

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Synthesis and Reactivity of 2‐Aroylbenzoic Acids, III. 2‐(4‐hydroxy‐3,5‐dimethylbenzoyl)benzoic Acid

Author(s) -

Rumiński Jan K.

Publication year - 1983

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19831160314

Subject(s) - chemistry , phthalide , benzoic acid , phthalic anhydride , yield (engineering) , reactivity (psychology) , medicinal chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology , materials science , metallurgy

Friedel‐Crafts 2‐carboxbenzoylation of 2,6‐xylenol with phthalic anhydride resulted in the formation of a new p ‐acylphenol type compound: 2‐(4‐hydroxy‐3,5‐dimethylbenzoyl)benzoic acid ( 1 ) (74% yield). Similar reactions of 2,6‐xylenol with tetrabromo‐ and tetrachlorophthalic anhydride gave the benzoic acid derivatives 13 and 14 , respectively. Another practical and efficient (93%) method for preparation of compound 1 was semi‐Stieglitz rearrangement of the known 3,3‐bis(4‐hydroxy‐3,5‐dimethylphenyl)phthalide ( 9 ). Reactions of the acid 1 have been investigated, leading to its derivatives 2–12 .

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