Ethylene Glycol → 2-(4-tert-Butyl-3-hydroxy-2,6-dimethylphenyl)acetic acid

HRID 616527

Reaktionsgleichung

Reaktionsgleichung von HRID 616527
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[C:8](CC#N)=[C:7]([CH3:15])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].[OH-:17].[Na+].[CH2:19]([OH:22])[CH2:20]O>O>[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([CH2:20][C:19]([OH:22])=[O:17])=[C:7]([CH3:15])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 174Ethylene GlycolHCID 14798Sodium HydroxideHCID 1087564-tert-Butyl-3-hydroxy-2,6-xylylacetonitrile

Produkt 1

HCID 203459052-(4-tert-Butyl-3-hydroxy-2,6-dimethylphenyl)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

65.1 grams of the compound of Example 3 was added with stirring to a solution of 36 grams of sodium hydroxide in 40 ml of ethylene glycol and 66 ml of water. The reaction mixture became homogenous at about 116° to 117° and was heated at this temperature for 2 hours. The reaction mixture was cooled by the addition of chopped ice and cold water to the reaction mixture to make a total volume of one liter. After clarifying the reaction mixture by filtration, the filtrate was made acid with concentrated aqueous hydrochloric acid, yielding a white precipitate, which was filtered, washed with cold water and dried. The product was then treated with rapid stirring at 50° C with about 800 ml of 6% sodium bicarbonate solution until carbon dioxide evolution stopped. The turbid solution was filtered free of a white solid by-product. (A). The clarified filtrate was made acid with concentrated hydrochloric acid while cooling, and the resulting white precipitate filtered. After washing with hot water and drying the product was obtained as a white powder melting at 161° to 165°.

Aufarbeitung

  1. custombecame homogenous at about 116° to 117°
  2. temperaturewas heated at this temperature for 2 hours
  3. filtrationby filtration
  4. customyielding a white precipitate, which
  5. filtrationwas filtered
  6. washwashed with cold water
  7. customdried
  8. additionThe product was then treated
  9. filtrationThe turbid solution was filtered free of a white solid by-product
  10. temperaturewhile cooling
  11. filtrationthe resulting white precipitate filtered
  12. washAfter washing with hot water
  13. customdrying the product

Quellen und Nachweise

ORD-Eintrag
ord-a87ac562427a47849c689a446715abb0
Quelldatensatz
uspto-grants-1978_02
Patentnummer
US04075161

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