Hydrochloric Acid → Citral

HRID 48548

Reaktionsgleichung

Reaktionsgleichung von HRID 48548
[CH3:1]/[C:2](/[CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])=[CH:3]\[CH2:4][OH:5].CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].[N+](C1C=CC=CC=1C=O)([O-])=O.Cl>C1C=CC=CC=1.C(OCC)(=O)C>[CH3:1]/[C:2](/[CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])=[CH:3]\[CH:4]=[O:5]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 111012-NitrobenzaldehydeHCID 11143Aluminum isopropoxideHCID 637566Geraniol

Produkt 1

HCID 638011CitralAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(2E)-3,7-Dimethyl-2,6-octadien-1-ol (310 mg, 2.0 mmol) was dissolved in benzene (1 mL), added with aluminum isopropoxide (40 mg, 0.1 eq, 0.20 mmol) and 2-nitrobenzaldehyde (390 mg, 1.3 eq, 2.6 mmol) and stirred at room temperature for 1 hour and 30 minutes. The reaction mixture was added with ethyl acetate and made acidic with addition of 2 N hydrochloric acid, and then the organic layer was separated. Subsequently, the organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to obtain 280 mg (yield: 93%, E:Z=87:13) of the title compound as yellow oil.

Aufarbeitung

  1. customthe organic layer was separated
  2. washSubsequently, the organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1)

Quellen und Nachweise

ORD-Eintrag
ord-4ae0b0b497a0479da954c0a821b1facd
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703527B2

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