Sulfuric Acid → 3,7-Dimethyloct-3-enoic acid

HRID 392843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 392843
S(=O)(=O)(O)[OH:2].[CH3:6]/[C:7](=[CH:11]\[CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])/[CH2:8][CH2:9][OH:10]>O.CC(C)=O.O.O.O.[Cr]>[CH3:6][C:7](=[CH:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:8][C:9]([OH:2])=[O:10]

Komponenten

6

Edukt 2

HCID 1118Sulfuric AcidHCID 22661166HCID 22661166, Verbindung

Produkt 1

HCID 713655083,7-Dimethyloct-3-enoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 14787Chromium trihydroxideKatalysatorHCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 8.84 g (88.4 mmol, 3 eq) of chromium VI oxide in 25 mL of water in the presence of 8.2 mL of 95% sulphuric acid is added to a solution of 4.6 g (29.5 mmol, 1 eq) of (E)-3,7-dimethyloct-3-enol in 250 mL of acetone, at 0° C., while maintaining the temperature at 0° C. After addition, the reaction mixture is stirred for 15 minutes at 0° C. and the reaction is then quenched by adding 250 mL of water. The reaction medium is extracted with 2×250 mL of diethyl ether. The organic phases are combined, washed with saturated sodium chloride solution and dried over anhydrous sodium sulphate, and the residue is then filtered through silica gel: eluent (95/5→75/25 Cy/EtOAc).

Aufarbeitung

  1. additionAfter addition
  2. customthe reaction is then quenched
  3. additionby adding 250 mL of water
  4. extractionThe reaction medium is extracted with 2×250 mL of diethyl ether
  5. washwashed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationthe residue is then filtered through silica gel

Quellen und Nachweise

ORD-Eintrag
ord-c8de4d884ec946e2a73d0ce20047b62b
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06803382B2

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