Pyridine → 5-Chloro-2-(2,4-dichlorophenoxy)phenyl 2-octanoyloxy-1-(octanoyloxymethyl)ethyl glutarate

Participants

Reaction Steps

A solution of 2-hydroxy-3-octanoyloxy-propyl octanoate (7.0 g.) and pyridine (1.5 g.) in chloroform (100 ml.) was treated dropwise at 0°-5° C. with a solution of 5-chloro-2-(2,4-dichlorophenoxy)phenyl 4-chloroformylbutyrate (A) (8.4 g.). The reaction mixture was then stirred at ambient temperature for 1 hour and diluted with ether (300 ml.) and water (200 ml). The organic phase was separated, washed successively with 2M hydrochloric acid (50 ml.), saturated sodium bicarbonate solution (3×50 ml.), and then dried (MgSO4) and evaporated. The residual oil was purified by chromatography on silica gel (50 g.) using a mixture of petrol 60-80 and ether (70:30 v/v) as eluant to give 5-chloro-2-(2,4-dichlorophenoxy)phenyl 2-octanoyloxy-1-(octanoyloxymethyl)ethyl glutarate as an oil.(9.1 g.); NMR (CDCl3): 0.9 (6H, t J=4.0 Hz, CH3), 1.1-7 (20H, complex m, CH2 ), 1.98 (2H,m, CH2), 2.2-2.7 (8H, complex, CO.CH2), 4.0-4.5 (4H,complex, CH2O), 5.25 (1H, br.t J=4.5 Hz, CH), 6.75-7.55 (6H,complex, aromatic H)ppm; mass spectrum (major diagnostic peaks): m/e 585 (16%) [M-0.CO(CH2)6CH3 ], 441. (21%), 385 (12%), 327 (100%), 288 (10%), 201 (10%), 127 (46%).

Provenance & Evidence