Sulfuric Acid → Nerol

HRID 918558Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 918558
[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O.[CH3:12]/[C:13](/[CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])=[CH:14]/[C:15](OC)=[O:16].O.[OH-].[Na+]>O1CCCC1.O.C(OCC)C>[CH3:12]/[C:13](/[CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])=[CH:14]/[CH2:15][OH:16]

Komponenten

8

Edukt 4

HCID 1118Sulfuric AcidHCID 5365912Methyl nerateHCID 21226445Aluminium lithium hydrideHCID 23719242Sodium hydroxide--water (1/1/1)

Produkt 1

HCID 643820Nerol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 10 ml. of 1 M lithium aluminum hydride in tetrahydrofuran, cooled to 0°, is added, dropwise, 0.28 ml. of 18 M sulfuric acid. The addition should be made at a rate such that the temperature remains at or below about +15°. After the addition is complete, the reaction mixture is stirred for 20 minutes and 0.55 grams of methyl (Z)-3,7-dimethylocta-2,6-dienoate is added. The reaction is allowed to proceed for about 3 hours while keeping the temperature between 0° and +5°. Then 20 ml. of ethyl ether is added, followed successively by 0.4 ml. of water, 0.4 ml. of a 15% sodium hydroxide water solution, and 1.2 ml. of water. The mixture then is filtered and the solid remaining is washed with ethyl ether. The organic filtrate is dried over sodium sulphate, filtered and evaporated under reduced pressure to yield, as an oil, (Z)-3,7-dimethylocta-2,6-dien-1-ol.

Aufarbeitung

  1. additionis added
  2. additionThe addition
  3. custombelow about +15°
  4. additionAfter the addition
  5. waitto proceed for about 3 hours
  6. customthe temperature between 0° and +5°
  7. filtrationThe mixture then is filtered
  8. washthe solid remaining is washed with ethyl ether
  9. dry with materialThe organic filtrate is dried over sodium sulphate
  10. filtrationfiltered
  11. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-df4fbab709214bdfaa647e6c16a60e38
Quelldatensatz
uspto-grants-1976_07
Patentnummer
US03971827

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