Toluene → 1-(3,4-Bis-benzyloxy-phenyl)-cyclopropanecarbonitrile

Participants

Reaction Conditions

Reaction Steps

To a mixture of (n-C4H9)4NBr (0.50 g, 1.5 mmol), toluene (7 mL) and (3,4-bis-benzyloxy-phenyl)-acetonitrile (14 g, 42 mmol) in NaOH (50 g) and H2O (50 mL) was added BrCH2CH2Cl (30 g, 0.21 mol). The reaction mixture was stirred at 50° C. for 5 h before being cooled to room temperature. Toluene (30 mL) was added and the organic layer was separated and washed with H2O, brine, dried over anhydrous MgSO4, and concentrated. The residue was purified by column on silica gel (petroleum ether/ethyl acetate 10:1) to give 1-(3,4-bis-benzyloxy-phenyl)-cyclopropanecarbonitrile (10 g, 66%). 1H NMR (DMSO 300 MHz) δ 7.46-7.30 (m, 10 H), 7.03 (d, J=8.4 Hz, 1 H), 6.94 (d, J=2.4 Hz, 1 H), 6.89 (dd, J=2.4, 8.4 Hz, 1 H), 5.12 (d, J=7.5 Hz, 4H), 1.66-1.62 (m, 2 H), 1.42-1.37 (m, 2 H).

Provenance & Evidence