Reaction #1934482

Reaction equation

Toluene

toluene

(3,4-bis-benzyloxy-phenyl)-acetonitrile

BrCH2CH2Cl

→

1-(3,4-bis-benzyloxy-phenyl)-cyclopropanecarbonitrile

Yield 66.0%

Solvents

NaOH

H2O

Conditions

Workup

1. 1
   Temperaturebefore being cooled to room temperature
2. 2
   Otherthe organic layer was separated
3. 3
   Washwashed with H2O, brine
4. 4
   Dryingdried over anhydrous MgSO4
5. 5
   Concentrationconcentrated
6. 6
   OtherThe residue was purified by column on silica gel (petroleum ether/ethyl acetate 10:1)

Procedure

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, 10H), 7.03 (d, J=8.4 Hz, 1H), 6.94 (d, J=2.4 Hz, 1H), 6.89 (dd, J=2.4, 8.4 Hz, 1H), 5.12 (d, J=7.5 Hz, 4H), 1.66-1.62 (m, 2H), 1.42-1.37 (m, 2H).

Source