Ortho-directed lithiation of omega-phenoxy alcohols

omega-Phenoxy alcohols, PhO(CH2)(n)OH (n = 2-7), have been subjected to met alation with 2 equiv of n-butyllithium in tetrahydrofuran/methylcyclohexane solvent. Reaction of the resulting lithiated compounds with carbon dioxide (n = 2-7), benzaldehyde (n = 2-6), benzophenone (n = 2, 3), dimethylformam ide (n = 2), ethyl formate (n = 2), and chlorodiphenylphosphine (n = 3) aff orded the corresponding ortho-substituted hydroxyalkoxybenzenes in yields r anging from 45 to 83%. The synthesis is also reported of five new bis[o-(om ega-hydroxyalkoxy)phenyl]mercury compounds (n = 2-6), four crystal structur es of which have been determined.