4-Tert-butylcyclohexane-1-carboxylic acid → 4-tert-Butylcyclohexylmethanol

HRID 892162

Reaktionsgleichung

Reaktionsgleichung von HRID 892162
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11](O)=[O:12])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:1]([CH:5]1[CH2:6][CH2:7][CH:8]([CH2:11][OH:12])[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

3

Edukt 1

HCID 1367594-Tert-butylcyclohexane-1-carboxylic acid

Produkt 1

HCID 827594-tert-Butylcyclohexylmethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a cooled (0° C.) solution of 4-tert-butylcyclohexane-carboxylic acid (3.00 g, 16.3 mmoles) in THF (30 mL) is slowly added a THF solution of borane-THF complex (1.0M, 21.2 mL, 21.2 mmoles). The solution is stirred at room temperature for 18 hours, then quenched with 2N HCl solution (30 mL), and extracted with EtOAc. The organic layer is isolated, washed with 1N NaOH, dried over sodium sulfate, and concentrated to yield the title compound as a clear oil. 1H NMR (300 MHz, CDCl3): δ 2.06 (d, 2H), 1.82 (m, 4H), 1.52 (m, 2H), 0.88 (m, 4H), 0.83 (s, 9H).

Aufarbeitung

  1. customquenched with 2N HCl solution (30 mL)
  2. extractionextracted with EtOAc
  3. customThe organic layer is isolated
  4. washwashed with 1N NaOH
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a6bf99dfdd46429099e8362ac7e4f668
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07005440B1

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