Hydrochloric Acid → 3-(1-Pyrrolidinyl)phenol

Participants

Reaction Conditions

Reaction Steps

7 g (30 mmol) of 1-Bromo-3-methoxymethoxy-benzene from step A and 2.5 g (35 mmol) of pyrrolidine were dissolved under argon in 60 mL of toluene. Then, 0.15 g (0.3 mmol) of bis(tri-t-butylphosphine)palladium(0), 2.5 g KOH und 0.6 g (0.15 mmol) cetyltrimethylammoniumbromid were added, and the reaction mixture was heated at 80° C. At the end of the reaction, the reaction mixture was poured into 200 mL of ethyl acetate, and the organic phase was extracted with 1N sodium hydroxide solution and then dried with magnesium sulfate. The solvent was distilled off in a rotary evaporator, and the residue was purified on silica gel using heptane/ethyl acetate (8/0.8). The product thus obtained was dissolved in 15 mL of ethanol and mixed with 10 mL of a 2.9 molar solution of ethanolic hydrochloric acid. The reaction mixture was then heated at 55° C. At the end of the reaction, the precipitate was filtered off, washed with ethanol, and then dried.

Provenance & Evidence