Sodium Hydroxide → 2-(4-tert-Butylcyclohexyl)acetic acid

HRID 365649

Reaktionsgleichung

Reaktionsgleichung von HRID 365649
C[O:2][C:3](=[O:15])[CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:7][CH2:6]1.[OH-].[Na+]>CO>[C:11]([CH:8]1[CH2:9][CH2:10][CH:5]([CH2:4][C:3]([OH:15])=[O:2])[CH2:6][CH2:7]1)([CH3:14])([CH3:12])[CH3:13]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 12808867Methyl 2-(4-tert-butylcyclohexyl)acetate

Produkt 1

HCID 41507362-(4-tert-Butylcyclohexyl)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

(4-tert-Butylcyclohexyl)acetic acid methyl ester (9.81 g, 46.5 mmol) was dissolved in methanol 950 ml) and cooled on an ice bath. 2M Sodium hydroxide solution (50 ml, 100 mmol) was added with stirring. When addition was complete the reaction mixture was allowed to warm to room temperature and was stirred overnight. The methanol was evaporated in vacuo and the remaining aqueous phase was acidified to pH1 with 1M hydrochloric acid. The aqueous phase was then extracted with ethyl acetate(3x). The organic extracts were combined, dried over magnesium sulphate, filtered and evaporated to give a white solid, (8.66 g, 94%). 1H-NMR δ (CDCl3) (as a mixture of cis-trans isomers), 2.43 (0.1 H, d, J=8Hz), 2.24 (0.9H, d, J =7 Hz), 1.92-1.47 (5H, m), 1.18-0.90 (5H, m) and 0.87 (9H, s).

Aufarbeitung

  1. temperaturecooled on an ice bath
  2. additionWhen addition
  3. stirringwas stirred overnight
  4. customThe methanol was evaporated in vacuo
  5. extractionThe aqueous phase was then extracted with ethyl acetate(3x)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customto give a white solid, (8.66 g, 94%)

Quellen und Nachweise

ORD-Eintrag
ord-ab7d9ffcf18c4cf18139033981a84944
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06127427

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