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20.2.10.1.1.3 Variation 3: Carboxylation of Phenols by Carbon Tetrachloride

DOI: 10.1055/sos-SD-020-00506

Yoon, T. P.; Jacobsen, E. N.Science of Synthesis, (200720535.

Treatment of a phenol, such as 3, with carbon tetrachloride and copper powder under alkaline conditions results in the formation of hydroxy acids, e.g. 4 (Scheme 3).[‌13‌] The regioselectivity of this process is generally lower than that observed in the KolbeSchmitt reaction, although the use of a cyclodextrin catalyst (β-CD; Scheme 3) can improve the selectivity to provide very good yields of the para-isomer, e.g. 4-hydroxybenzoic acid (5).[‌14‌]

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