Exclusive ortho. alpha.-chloroacetylation of phenols

T Toyoda, K Sasakura, T Sugasawa

Index: Toyoda, Tatsuo; Sasakura, Kazuyuki; Sugasawa, Tsutomu Journal of Organic Chemistry, 1981 , vol. 46, # 1 p. 189 - 191

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Citation Number: 20

Abstract

Resorcinol (1) can be easily acylated on the aromatic ring by treatment with nitriles in the presence or absence of Lewis acids such as zinc chloride or aluminum chloride in acidic medium (Houben-Hoesch reaction), while in contrast, phenol (2) itself can not be ring- acylated by a similar treatment, giving only a salt of iminomethyl phenyl ether (3)(Scheme I). Moreover, an attempt at thermal rearrangement of 3 gives no ring-acylated product by ...