Benzoyl chloride → 2-(2-Hydroxy-4-isopropylphenyl)-1,3-dioxo-2,3-dihydro-1H-inden-2-yl benzoate

HRID 527119

Reaktionsgleichung

Reaktionsgleichung von HRID 527119
[OH:1][C:2]1([C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][C:14]=2[OH:22])[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12].[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C>C(Cl)Cl.CC(NP(OC1C=CC(Cl)=CC=1Cl)(OC)=S)C>[C:23]([O:1][C:2]1([C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:20])[CH3:21])=[CH:15][C:14]=2[OH:22])[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

6

Edukt 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 30544341H-Indene-1,3(2H)-dione, 2-hydroxy-2-(2-hydroxy-4-(1-methylethyl)phenyl)-

Produkt 1

HCID 714766762-(2-Hydroxy-4-isopropylphenyl)-1,3-dioxo-2,3-dihydro-1H-inden-2-yl benzoateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9299ZytronKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-hydroxy-2-(2-hydroxy-4-isopropyl-phenyl)-indan-1,3-dione (1.00 g, 3.37 mmol) was completely dissolved in anhydrous methylene chloride (20 ml). This solution was added with benzoyl chloride (0.94 g, 6.74 mmol), triethylamine (0.41 g, 4.04 mmol), and DMPA (0.01 g), followed by heating 24 hrs under reflux. After the reaction mixture was concentrated, extracted with dichloromethane, and the organic layer was concentrated and purified using column chromatography (ethylacetate:hexane=1:4) to afford the title compound (0.81 g, 14%).

Aufarbeitung

  1. temperatureby heating 24 hrs
  2. temperatureunder reflux
  3. concentrationAfter the reaction mixture was concentrated
  4. extractionextracted with dichloromethane
  5. concentrationthe organic layer was concentrated
  6. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-615bee9a0f734bd7bbb05fff6487ce3d
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346749B2

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