Hydrochloric Acid → 1,1'-Binaphthalene, 2,2'-dimethyl-

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Reaction Conditions

Reaction Steps

2-Methyl-1-naphthylmagnesium bromide prepared according to Example 1 in toluene is added in the absence of air and moisture to a suspension, heated to 70° to 80° C., of 31.0 g (0.14 mol) of 1-bromo-2-methylnaphthalene, 0.0014 mol of the phosphine of the formula (I) 1,4-bis(diphenylphosphino)butane; 2,2'-bis(diphenylphosphinomethoxy)-1,1'-binaphthyl! or 0.0028 mol of the phosphine of the formula (II) (triphenylphosphine) and 0.31 g (0.0014 mol) of palladium(II) acetate in 50 ml of toluene. The mixture is then heated at 80° C. for another hour, cooled to 25° C., and 100 ml of water and 50 ml of 2N hydrochloric acid are added in succession to the reaction mixture. The phases are separated, the aqueous phase is extracted with 50 ml of toluene, and the combined organic phases are concentrated in vacuo. Distillation of the oily, brown residue in a high vacuum gives a pale yellow oil having a boiling point of 175° to 180° C./0.1 to 0.2 mbar. The yields can be found in Table 1 below.

Provenance & Evidence