100.8 g (1.2 mols) of diketene were added dropwise at -30° C to 0.5 l of anhydrous hydrofluoric acid and a mixture of 0.6 mol of tetrahydronaphthalene and 0.6 mol of commercial grade dodecyl-benzene were dropped in. After stirring for 12 hours at room temperature, the reaction mixture was stirred into 3 l of icewater. After extraction with methylene chloride, washing with water to remove the acid from the organic phase and distillation of the methylene chloride, distillation of the reaction mixture yielded 86 % of acetoacetyl-tetrahydronaphthalene boiling at 135° C under 0.5 terr and 77 g (40%) of acetoacetyl-dodecyl-benzene boiling at 160° C under 0.5 torr as found by gas chromatographic determination of the fractions.
