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Diethyl Ether → [4-(Acetyloxy)-2-hydroxy-3-propylphenyl][2(acetyloxy)phenyl]methanone

HRID 2292214
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2292214
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([OH:11])[CH:5]=[CH:4][C:3]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20])=[O:13].C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[C:37](OC(=O)C)(=[O:39])[CH3:38].[CH2:44]([O:46]CC)[CH3:45]>>[C:37]([O:11][C:6]1[CH:5]=[CH:4][C:3]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][C:44](=[O:46])[CH3:45])=[O:13])=[C:2]([OH:1])[C:7]=1[CH2:8][CH2:9][CH3:10])(=[O:39])[CH3:38]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 14421654HCID 14421654, Verbindung

Produkt 1

HCID 21277006[4-(Acetyloxy)-2-hydroxy-3-propylphenyl][2(acetyloxy)phenyl]methanone

Versuchsvorschrift

Five grams of (2,4-dihydroxy-3-propylphenyl)- (2-hydroxyphenyl)methanone, 5.63 ml of triethylamine, and approximately 50 mg of dimethylaminopyridine were dissolved in 50 ml of diethyl ether at 0° C. Acetic anhydride (3.8 ml) was added dropwise. After stirring for 1 hour, the reaction mixture was partitioned between diethyl ether and water. The organic layer was separated, washed with 1N hydrochloric acid, a saturated solution of sodium bicarbonate, and a saturated solution of sodium chloride, dried over magnesium sulfate, and concentrated in vacuo. Purification by high pressure liquid chromatography over silica gel eluting with a 10-25% ethyl acetate in hexane gradient and concentration of the appropriate fractions provided 2.6 g of the desired title product as an oil.

Aufarbeitung

  1. customthe reaction mixture was partitioned between diethyl ether and water
  2. customThe organic layer was separated
  3. washwashed with 1N hydrochloric acid
  4. dry with materiala saturated solution of sodium bicarbonate, and a saturated solution of sodium chloride, dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by high pressure liquid chromatography over silica gel eluting with a 10-25% ethyl acetate in hexane gradient and concentration of the appropriate fractions

Quellen und Nachweise

ORD-Eintrag
ord-b506f0a93f454478842c6ee5fb111de7
Quelldatensatz
uspto-grants-1989_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04801616

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