Triclosan → 5-Chloro-2-(2,4-dichlorophenoxy)phenyl 2-octanoyloxy-1-(octanoyloxymethyl)ethyl adipate

HRID 279907

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])=[C:6]([OH:8])[CH:7]=1.[C:18](Cl)(=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][C:23](Cl)=[O:24].[C:28]([O:37][CH2:38][CH:39]([OH:51])[CH2:40][O:41][C:42](=[O:50])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])(=[O:36])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>>[C:18]([O:8][C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[Cl:17])(=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:51][CH:39]([CH2:40][O:41][C:42](=[O:50])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:38][O:37][C:28](=[O:36])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:24]

Participants

Reactant 3

HCID 5564Triclosan

HCID 61034Adipoyl chloride

HCID 1509111,3-Dioctanoyl glycerol

Product 1

HCID 537986175-Chloro-2-(2,4-dichlorophenoxy)phenyl 2-octanoyloxy-1-(octanoyloxymethyl)ethyl adipateYield 33%

Procedure

Using a similar procedure to that described in Example 6, but using 5-chloro-2-(2,4-dichlorophenoxy)phenol, adipoyl dichloride and 2-hydroxy-3-octanoyloxypropyl octanoate as starting materials, there was obtained 5-chloro-2-(2,4-dichlorophenoxy)phenyl 2-octanoyloxy-1-(octanoyloxymethyl)ethyl adipate as an oil in 33% yield; NMR (CDCL3): 0.85 (6H, br.s, CH3), 1.25+1.65 (24H, br.s, CH2), 2.3 (8H, m, COCH2), 4.2 (4H, m, OCH2), 5.25 (1H, m, CH), 6.6-7.5 (6H, complex, aromatic H)ppm.

Sources & evidence

ORD record: ord-962d4d809c1646448aff1daaf2ff3aae
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04587262

Linked notes

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