RI 2912 The 1, 3 Dimethyl-2-Phenoxyacetic Acid

As a preliminary step in a recent study4 of the phenols present in a low-temperature tar, the writers prepared the hydroxyacetic derivatives of the simpler available members of the phenol series in order to obtain material to assist in fixing the identity of similar derivatives obtained from the phenols of the tar. When comparing the melting points of the pure derivatives we had made with those given in the literature we were unable to find the characteristics of one of the xylenol derivatives which we had prepared--namely the 1, 3 dimethyl-2-phenoxyacetic acid, In the belief that the compound does not appear in the literature we are presenting these notes on its preparation and its melting point. The hydroxyacetic derivatives are easily prepared and in good yield, and are useful in studying mixtures of phenols. The 1, 3 dimethyl-2-phenoxyacetic acid makes the fifth of the six isomeric derivatives to be reported in the literature. Gluud and Breuer report the preparation of the 1, 3, 4, the 1, 4, 2, and the 1, 2, 4 derivatives. A fourth isomer-¬the symmentrical 1, 3, 5--has been reported by Schutz6, although no record of it occurs in the indexes. The remaining derivative--the 1, 2, 8-has not, been found and it is now being synthesized in the Organic Chemistry Laboratory of the. Pittsburgh Experiment Station. It is true, however, that from a phenolic fraction boiling 215.9 to 2180 isolated from natural petroleum, Tanaka and Kobayashi7 obtained a hydroxyacetic derivative melting at 103.3°. They state that this is the 1, 2, dime ethyl-3-phenoxyacetic acid but present no evidence for the assertion. The known derivatives are summarized in Table 1 following;