A Simple Method for the Preparation of Dichlorocatechols.

Article abstract of DOI:10.1016/0045-6535(94)90206-2

Dichlorocatechols (DCC) are common metabolites in the aerobic degradation of dichlorobenzenes. Their synthesis is therefore possible either enzymatically, or chemically by several two-step-synthesis starting from cycloalkanones or suitable dichlorophenols. A modified ultrasonic Reimer/Tiemann reaction and subsequent Dakin oxidation was used to prepare 3,5-DCC and 4,5-DCC. A new UV-photoradical single step synthesis of 3,4-dichlorocatechol as well as 3,6-dichlorocatechol is described in detail. Mass spectral and ¹³C-NMR spectral data of all four dichlorocatechol isomers are presented.