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

HRID 279908

反応式

HRID 279908 の反応式
[C:1]([O:9][CH:10]([CH2:22][O:23][C:24](=[O:32])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:11][O:12][C:13](=[O:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])(=[O:8])[CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH:46]1[C:51]([Cl:52])=[CH:50][C:49](O)=[C:48]([O:54][C:55]2[CH:56]=[CH:57][C:58]([Cl:62])=[CH:59][C:60]=2[Cl:61])[CH:47]=1>C1(C)C=CC=CC=1>[C:5]([O:7][C:49]1[CH:50]=[C:51]([Cl:52])[CH:46]=[CH:47][C:48]=1[O:54][C:55]1[CH:56]=[CH:57][C:58]([Cl:62])=[CH:59][C:60]=1[Cl:61])(=[O:6])[CH2:4][CH2:3][CH2:2][C:1]([O:9][CH:10]([CH2:22][O:23][C:24](=[O:32])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:11][O:12][C:13](=[O:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:8]

参加物

5

反応物 3

HCID 5564TriclosanHCID 9845Trifluoroacetic anhydrideHCID 233228862-Octanoyloxy-1-(octanoyloxymethyl)ethyl hydrogen glutarate

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

2-Octanoyloxy-1-(octanoyloxymethyl)ethyl hydrogen glutarate (4.22 g.) was dissolved in dry toluene (40 ml.) and stirred with trifluoroacetic anhydride (5.2 ml.) for 2.5 hours. Triclosan (2.67 g.) was added and the mixture stirred for a further 20 hours. The solution obtained was washed successively with water (2×40 ml.), saturated sodium bicarbonate solution (2×40 ml.) and saturated brine (40 ml.). The organic phase was dried (MgSO4) and evaporated. The oil obtained was chromatographed on silica gel using methylene chloride as eluant to give 5-chloro-2-(2,4-dichlorophenoxy)phenyl 2-octanoyloxy-1-(octanoyloxymethyl)ethyl glutarate as an oil, having the same NMR and mass spectra as described for the ester in Example 1.

後処理

  1. customThe solution obtained
  2. washwas washed successively with water (2×40 ml.), saturated sodium bicarbonate solution (2×40 ml.) and saturated brine (40 ml.)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated
  5. customThe oil obtained
  6. customwas chromatographed on silica gel

出典と根拠

ORDレコード
ord-c678961920084f3d824492d952a09995
出典データセット
uspto-grants-1986_05
特許番号
US04587262

関連ノート

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