Hydroquinone → 4-(6-(2-Tetrahydropyranyl)oxyhexyloxy)phenol

HRID 28312

Reaktionsgleichung

Reaktionsgleichung von HRID 28312
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1.[C:15]1([CH:22]=[CH:21][C:19]([OH:20])=[CH:18][CH:17]=1)[OH:16].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.CS(C)=O>[O:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH:9]1[O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:16][C:15]1[CH:22]=[CH:21][C:19]([OH:20])=[CH:18][CH:17]=1

Komponenten

7

Edukt 4

HCID 785HydroquinoneHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 3298032-(6-Chlorohexyloxy)tetrahydro-2H-pyran

Produkt 1

HCID 178385764-(6-(2-Tetrahydropyranyl)oxyhexyloxy)phenolAusbeute 82,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 10 g of 2-(6-chlorohexyloxy)tetrahydropyrane, 25 g of hydroquinone, 31 g of potassiumcarbonate, 0.752 g of potassiumiodide and 250 ml of dimethylsulfoxide was allowed to react for 4 days at 80° C. Subsequently, the reaction mixture was cooled to room temperature and after addition of water extracted with ether. The organic phase was then dried over sodium sulphate, filtered and concentrated to dryness. Chromatography on silica with 10% ethylacetate in toluene gave 11 g of product as a yellowish oil.

Aufarbeitung

  1. customto react for 4 days at 80° C
  2. extractionextracted with ether
  3. dry with materialThe organic phase was then dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-7f83b244a5014c8fbe2f48fda79a83a5
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419620B2

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