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

HRID 279906

Reaction equation

HRID 279906 reaction equation
[C:1]([O:10][CH2:11][CH:12]([OH:24])[CH2:13][O:14][C:15](=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].N1C=CC=CC=1.Cl[C:32]([CH2:34][CH2:35][CH2:36][C:37]([O:39][C:40]1[CH:45]=[C:44]([Cl:46])[CH:43]=[CH:42][C:41]=1[O:47][C:48]1[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][C:49]=1[Cl:55])=[O:38])=[O:33]>C(Cl)(Cl)Cl.CCOCC.O>[C:37]([O:39][C:40]1[CH:45]=[C:44]([Cl:46])[CH:43]=[CH:42][C:41]=1[O:47][C:48]1[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][C:49]=1[Cl:55])(=[O:38])[CH2:36][CH2:35][CH2:34][C:32]([O:24][CH:12]([CH2:13][O:14][C:15](=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:11][O:10][C:1](=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[O:33]

Participants

7

Reactant 3

HCID 1049PyridineHCID 1509111,3-Dioctanoyl glycerolHCID 536851365-Chloro-2-(2,4-dichlorophenoxy)phenyl 4-chloroformylbutyrate

Product 1

HCID 233228885-Chloro-2-(2,4-dichlorophenoxy)phenyl 2-octanoyloxy-1-(octanoyloxymethyl)ethyl glutarate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

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%).

Workup

  1. customThe organic phase was separated
  2. washwashed successively with 2M hydrochloric acid (50 ml.), saturated sodium bicarbonate solution (3×50 ml.)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residual oil was purified by chromatography on silica gel (50 g.)
  6. additiona mixture of petrol 60-80 and ether (70:30 v/v) as eluant

Sources & evidence

ORD record
ord-41eb8bcf7b8147b19dc74876dee06d48
Source dataset
uspto-grants-1986_05
Patent number
US04587262

Linked notes

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