Sodium Hydroxide → 5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

HRID 654211

Reaktionsgleichung

Reaktionsgleichung von HRID 654211
[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14](=[O:16])C)[CH:5]=[CH:4][C:3]1=2.Cl[O-].[Na+].[OH-:21].[Na+]>O1CCOCC1>[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]([OH:16])=[O:21])[CH:5]=[CH:4][C:3]1=2

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 27475621-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-oneHCID 23665760Sodium Hypochlorite

Produkt 1

HCID 2276385,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 3.8 g (16.5 mmol) of 5,5,8,8-tetramethyl-2-acetyl-5,6,7,8-tetrahydronaphthalene from the preceding Example 3, 70 ml of 5.25% aqueous sodium hypochlorite (49 mmol), 25 ml of aqueous 2N NaOH and 30 ml of dioxane was heated at 60°-70° C. for 2 hours. The mixture was allowed to cool and the oily organic layer removed. Then the aqueous layer was washed with two portions of ether. The aqueous layer was then treated with sodium metabisulfite solution until the solution was negative to the potassium iodide/starch test. The aqueous layer was then cooled and acidified with H2SO4. The resultant white precipitate was collected by filtration and washed with water. This crude product was further purified by recrystallization from an ethanol/water mixture to give the title compound as a white, crystalline solid.

Aufarbeitung

  1. temperaturewas heated at 60°-70° C. for 2 hours
  2. temperatureto cool
  3. customthe oily organic layer removed
  4. washThen the aqueous layer was washed with two portions of ether
  5. additionThe aqueous layer was then treated with sodium metabisulfite solution until the solution
  6. temperatureThe aqueous layer was then cooled
  7. filtrationThe resultant white precipitate was collected by filtration
  8. washwashed with water
  9. customThis crude product was further purified by recrystallization from an ethanol/water mixture

Quellen und Nachweise

ORD-Eintrag
ord-44211a7b665640548873524b5d2130de
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05130335

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