2-Cyclohexene-1-carboxaldehyde, 2,6,6-trimethyl- → 2,6,6-Trimethylcyclohex-2-ene-1-methanol

HRID 372612Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 372612
[BH4-].[Na+].[CH3:3][C:4]1[CH:9]([CH:10]=[O:11])[C:8]([CH3:13])([CH3:12])[CH2:7][CH2:6][CH:5]=1>C(O)C>[CH3:3][C:4]1[CH:9]([CH2:10][OH:11])[C:8]([CH3:13])([CH3:12])[CH2:7][CH2:6][CH:5]=1

Komponenten

4

Edukt 2

HCID 941432-Cyclohexene-1-carboxaldehyde, 2,6,6-trimethyl-HCID 4311764Sodium borohydride

Produkt 1

HCID 979322,6,6-Trimethylcyclohex-2-ene-1-methanolAusbeute 71,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a suspension of 1.25 g NaBH4 in 50 ml. 95% ethanol cooled in an ice bath was added dropwise with stirring 5.0 g alpha-cyclocitral which had been prepared as described in Example 1. When the addition was complete, the ice bath was removed and water was added to dissolve any remaining solids. The reaction mixture was then stirred overnight at room temperature. The solvent was removed at reduced pressure and the residue taken up in ether, washed with 1 N acetic acid, dilute sodium bicarbonate and water. The ether extract was dried over sodium sulfate and concentrated to give 3.6 g alpha-cyclogeraniol as a colorless oil of 95% purity by gas chromatographic analysis.

Aufarbeitung

  1. additionwas added dropwise
  2. customhad been prepared
  3. additionWhen the addition
  4. customthe ice bath was removed
  5. additionwater was added
  6. dissolutionto dissolve any remaining solids
  7. customThe solvent was removed at reduced pressure
  8. washwashed with 1 N acetic acid, dilute sodium bicarbonate and water
  9. extractionThe ether extract
  10. dry with materialwas dried over sodium sulfate
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d8f23aa72d334b6e9e4242040fde1b20
Quelldatensatz
uspto-grants-1978_05
Patentnummer
US04091823

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