4-Propylbenzoic acid → (E)-5-[4-(2-methoxycarbonylvinyl)benzoyloxy]-2-(4-propylbenzoyloxy)benzoic acid 11-(2-methylacryloyloxy)undecyl ester

HRID 479925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 479925
[CH3:1][C:2](=[CH2:42])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18](=[O:41])[C:19]1[CH:24]=[C:23]([O:25][C:26](=[O:39])[C:27]2[CH:32]=[CH:31][C:30](/[CH:33]=[CH:34]/[C:35]([O:37][CH3:38])=[O:36])=[CH:29][CH:28]=2)[CH:22]=[CH:21][C:20]=1[OH:40])=[O:4].[CH2:43]([C:46]1[CH:54]=[CH:53][C:49]([C:50](O)=[O:51])=[CH:48][CH:47]=1)[CH2:44][CH3:45].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[CH3:42][C:2](=[CH2:1])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18](=[O:41])[C:19]1[CH:24]=[C:23]([O:25][C:26](=[O:39])[C:27]2[CH:28]=[CH:29][C:30](/[CH:33]=[CH:34]/[C:35]([O:37][CH3:38])=[O:36])=[CH:31][CH:32]=2)[CH:22]=[CH:21][C:20]=1[O:40][C:50](=[O:51])[C:49]1[CH:53]=[CH:54][C:46]([CH2:43][CH2:44][CH3:45])=[CH:47][CH:48]=1)=[O:4]

Komponenten

6

Edukt 3

HCID 1376014-Propylbenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 20600092HCID 20600092, Verbindung

Produkt 1

HCID 69971169(E)-5-[4-(2-methoxycarbonylvinyl)benzoyloxy]-2-(4-propylbenzoyloxy)benzoic acid 11-(2-methylacryloyloxy)undecyl esterAusbeute 79,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

1.0 g (1.72 mmol) (E)-2-hydroxy-5-[4-(2-methoxycarbonylvinyl)benzoyloxy]benzoic acid 11-(2-methylacryloyloxy)undecyl ester, 0.37 g (2.24 mmol) 4-propylbenzoic acid and 58 mg (0.47 mmol) 4-dimethylaminopyridine were dissolved in 20 ml of dichloromethane. A suspension of 0.43g (2.24 mmol) N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride and 10 ml dichloromethane were added dropwise in the course of 45 minutes. After 65 hour at room temperature the reaction mixture was partitioned between dichloromethane and water; the organic phase was washed repeatedly with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. Chromatography of the residue on 120 g silica gel using cyclohexane:ethyl acetate 4:1 and subsequent crystallisation form 50 ml isopropyl alcohol yielded 0.99 g (79%) (E)-5-[4-(2-methoxycarbonylvinyl)benzoyloxy]-2-(4-propylbenzoyloxy)benzoic acid 11-(2-methylacryloyloxy)undecyl ester as white powder, m.p. (C/N) 86.8° C., cl.p (N/I) 102.8° C.

Aufarbeitung

  1. additionwere added dropwise in the course of 45 minutes
  2. customAfter 65 hour at room temperature the reaction mixture was partitioned between dichloromethane and water
  3. washthe organic phase was washed repeatedly with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-639bc5d284a2463980a82ae020e28012
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06649230B1

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