1-Phenylcyclohexane-1-carboxylic acid → 1-Phenylcyclohexanemethanol

HRID 1270447

Reaktionsgleichung

Reaktionsgleichung von HRID 1270447
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([C:13]2([C:19](O)=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>>[C:7]1([C:13]2([CH2:19][OH:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

3

Edukt 2

HCID 708171-Phenylcyclohexane-1-carboxylic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 1985171-PhenylcyclohexanemethanolAusbeute 89,1 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of LAH (3.8 g, 0.1 mol) cooled to 0° C. was slowly added 1-phenyl-cyclohexanecarboxylic acid (10.2 g, 50.0 mmol). After stirring from 0° C. to rt overnight, the reaction mixture was quenched with H2O (3.8 mL), 15% NaOH (3.8 mL), H2O (11.4 mL) and filtered. The salt was washed with Et2O and the combined organic phase dried over anhydrous sodium sulfate to give (1-phenyl-cyclohexyl)-methanol (8.48 g, 89%) as a white solid. 1H NMR (CDCl3, 300 MHz) δ (ppm) 1.30–1.70 (9H, m), 2.15–2.36 (2H, m), 3.51 (2H, s), 7.20–7.27 (1H, m), 7.34–7.41 (4H, m). Mass Spec [M+H]+=191.1.

Aufarbeitung

  1. customthe reaction mixture was quenched with H2O (3.8 mL), 15% NaOH (3.8 mL), H2O (11.4 mL)
  2. filtrationfiltered
  3. washThe salt was washed with Et2O
  4. dry with materialthe combined organic phase dried over anhydrous sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-2966f8321386480fa7fa2921c2d972b8
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202253B2

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