Lithium Hydroxide → 2-Carboxy-2-(t-butyl)thiomethyl-1,2,3,4-tetrahydronaphthalene

HRID 1656046

Reaktionsgleichung

Reaktionsgleichung von HRID 1656046
[C:1]([C:5]1([CH2:15][S:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)([O:3]C)=[O:2].[OH-].[Li+]>CO.O>[C:1]([C:5]1([CH2:15][S:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)([OH:3])=[O:2]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 197899492-Carbomethoxy-2-(t-butyl)thiomethyl-1,2,3,4-tetrahydronaphthalene

Produkt 1

HCID 197899372-Carboxy-2-(t-butyl)thiomethyl-1,2,3,4-tetrahydronaphthaleneAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Dissolve 2-carbomethoxy-2-(t-butyl)thiomethyl-1,2,3,4-tetrahydronaphthalene (2.5 g, 8.6 mmol) in methanol (50 mL) and add 1N lithium hydroxide (15 mL, 15 mmol). Stir at reflux for 12 hours and at room temperature for an additional 12 hours. Dilute with water (10 mL) and concentrate in vacuo to 20 mL. Wash with ethyl ether and acidify the aqueous phase with 2N hydrochloric acid. Extract with methylene chloride (2×25 mL), dry (MgSO4) and evaporate the solvent in vacuo to give the title compound as a crystalline solid (2.37 g, 99%).

Aufarbeitung

  1. concentrationconcentrate in vacuo to 20 mL
  2. washWash with ethyl ether
  3. extractionExtract with methylene chloride (2×25 mL)
  4. dry with materialdry (MgSO4)
  5. customevaporate the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-10581ad776824abb8e98b36396b8a111
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05252601

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