In the presence of a tertiary amine, phenols underwent an abnormal Reimer-Tiemann reaction, i.e., the ratio of the para- and ortho-products was reversed. For example, phenol gave 60% yield of p-hydroxybenzaldehyde, 7% yield of o-hydroxybenzaldehyde and 1% of tarry materials. Whereas in the absence of the tertiary amines, the yield of para-, ortho-, and tarry materials under the optimum conditions were 8-11, 38-45 and 20% resp. The conditions of the abnormal Reimer-Tiemann reaction were studied in detail and a mechanism was proposed. o-Methylphenol, and o-methoxyphenol underwent the above abnormal Reimer-Tiemann reaction similarly.

Key words: PHENOL P, BENZALDEHYDE P, TERTIARY AMINE, CHLOROFORM, BUTANAMINE P, BENZALCOHOL, REIMER-TIEMANN