Lithium Hydroxide → 4-(Methoxycarbonyl)cyclohexane-1-carboxylic acid

HRID 349099

Reaktionsgleichung

Reaktionsgleichung von HRID 349099
[CH:1]1([C:11]([O:13]C)=[O:12])[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]1.[OH-].[Li+]>O1CCCC1.CO.O>[CH3:10][O:9][C:7]([CH:4]1[CH2:5][CH2:6][CH:1]([C:11]([OH:13])=[O:12])[CH2:2][CH2:3]1)=[O:8]

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 7198Dimethyl 1,4-cyclohexanedicarboxylate

Produkt 1

HCID 2968504-(Methoxycarbonyl)cyclohexane-1-carboxylic acidAusbeute 77,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

To a stirred solution of dimethyl cyclohexane-1,4-dicarboxylate (10.2 g, 51 mmol) in a mixture of 2:1:1 tetrahydrofuran/methanol/water (52 mL) was added lithium hydroxide (2.13 g, 51 mmol). The reaction mixture was stirred at room temperature for 18 h. The solvent was removed under reduced pressure and the residue was partitioned between diethyl ether and water. The aqueous layer was acidified to pH 4 with 1 N hydrochloric acid, and the precipitate collected, and dried under vacuum to afford 4-(methoxycarbonyl)cyclohexanecarboxylic acid (7.4 g): 1H NMR (300 MHz, CDCl3) δ 3.68 (s, 3H), 2.33–2.27 (m, 2H), 2.11–2.06 (m, 4H), 1.50–1.43 (m, 4H).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between diethyl ether and water
  3. customthe precipitate collected
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-43304f0fdc8f4b1eb1d65be76a622463
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176242B2

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