Hydrogen Peroxide → 2-(4-t-Butylphenyl)-3-hydroxy-4-methylcarbonylthiophene

HRID 239230Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 239230
CO.[C:3]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[C:17]([OH:18])=[C:16]([C:19]([CH3:21])=[O:20])[CH2:15][S:14]2)=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].OO.C1(C)C=CC=CC=1>O.CCCCCCC>[C:3]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:14][CH:15]=[C:16]([C:19]([CH3:21])=[O:20])[C:17]=2[OH:18])=[CH:11][CH:12]=1)([CH3:6])([CH3:4])[CH3:5]

Komponenten

7

Edukt 4

HCID 784Hydrogen PeroxideHCID 887Methanol2×HCID 1140TolueneHCID 44207041HCID 44207041, Verbindung

Produkt 1

HCID 442072892-(4-t-Butylphenyl)-3-hydroxy-4-methylcarbonylthiophene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8900HeptaneLösungsmittel

Reaktionsbedingungen

Temperatur
51 °C

Versuchsvorschrift

A solution having methanol (121.20 g) added to a 11.2 mass % methanol solution (539.0 g, 217.08 mmol) of 2-(4-t-butylphenyl)-3-hydroxy-4-methylcarbonyl-2,5-dihydrothiophene was heated to 51° C., and a 30 mass % hydrogen peroxide solution (61.6 g, 2.5 equivalent amounts) was dropwise added over a period of 30 minutes, followed by stirring at from 50 to 52° C. for 5 hours. Then, the solution was cooled to 25 to 30° C., and then toluene, heptane and water were added, followed by liquid separation. Then, to the obtained organic layer, a 7 mass % sodium hydrogencarbonate aqueous solution, toluene and heptane were added, followed by liquid separation, and further, the obtained organic layer was washed with a 3 mass % salt solution. The solvent was distilled off under reduced pressure from the obtained organic layer to give a 26.6 mass % solution of the desired product. To the obtained solution, methanol was added to adjust the concentration to 9 mass %, and the solution was heated to from 55 to 60° C. to dissolve the formed solid. To this solution, 24.2 g of water was further dropwise added, followed by stirring for 1 hour. Then, the solution was cooled to −10° C. and stirred for 1 hour. The formed crystals were subjected filtration to give the desired product as yellow crystals (44.2 g, yield: 73.9%).

Aufarbeitung

  1. temperatureThen, the solution was cooled to 25 to 30° C.
  2. customfollowed by liquid separation
  3. additionThen, to the obtained organic layer, a 7 mass % sodium hydrogencarbonate aqueous solution, toluene and heptane were added
  4. customfollowed by liquid separation
  5. washfurther, the obtained organic layer was washed with a 3 mass % salt solution
  6. distillationThe solvent was distilled off under reduced pressure from the obtained organic layer

Quellen und Nachweise

ORD-Eintrag
ord-34549bbd194542669472f3e5a124b56d
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642786B2

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