Toluene → 7-Phenyl-1-heptyl chloride

Participants

Reaction Steps

A solution of lithium tetrachlorocuprate [THF 33 L, lithium chloride (0.87 kg, 19.3 mol), cupric chloride (1.4 kg, 10.4 mol)] was added to a solution of benzylmagnesium chloride (160 L of 1.86M, 298 mol) in tetrahydrofuran at 15° C., and the mixture stirred for 30 min. Bromochlorohexane in toluene (85.5 kg of solution, 55% w/w by assay, 47.1 kg, 236 mol) was added over 3 h while maintaining the temperature between 15°-20° C. Stirring was continued for a further 1.25 h. 10% Ammonium chloride solution (263 L) was added over 1 h, maintaining the temperature below 30° C. The phases were separated and the organic phase further washed with ammonium chloride solution (170 L) and 20% sodium chloride solution (3×197 L). The organic solution was concentrated under vacuum to leave an oil (56.8 kg, 77% pure by HPLC assay, 88% corrected yield), which was distilled (b.p. 129°-132° C., 2 mbar) to yield the title compound (70%, 99% pure by GC assay).

Provenance & Evidence