A phenylene ether oligomer is prepared by a process that includes partially converting 2,6-dimethylphenol to 3,3',5,5'-tetramethyl-4,4'-dihydroxybiphenyl and/or 3,3',5,5'-tetramethyldiphenoquinone, converting the residual 2,6 dimethylphenol to poly(2,6-dimethyl-1,4-phenylene ether) and any 3,3',5,5'-tetramethyl-4,4'-dihydroxybiphenyl to 3,3',5,5'-tetramethyldiphenoquinone, and reacting the poly(2,6-dimethyl-1,4-phenylene ether) and 3,3',5,5'-tetramethyldiphenoquinone to form the phenylene ether oligomer. The preparation can be conducted without isolation of intermediates.