Acetic Acid → 2-Hexyl-5-tetradecylphenol

HRID 34850Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 34850
[OH:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:5]=[CH:4][C:3]=1[C:22](=O)[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C(O)(=O)C>[Pd].CO>[CH2:22]([C:3]1[CH:4]=[CH:5][C:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:7][C:2]=1[OH:1])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Komponenten

5

Edukt 2

HCID 176Acetic AcidHCID 148196731-(2-Hydroxy-4-tetradecylphenyl)-1-hexanone

Produkt 1

HCID 142562092-Hexyl-5-tetradecylphenolAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 16.99 g of 1-(2-hydroxy-4-tetradecylphenyl)-1-hexanone, 4 g of 5% palladium on carbon catalyst, 100 ml of glacial acetic acid and 50 ml of methanol was hydrogenated in a Parr apparatus for 24 hours. The mixture was filtered, the solvents removed and the residue dissolved in ether, washed with water and dried. This crude material was chromatographed on silica gel, eluting with hexane:ethyl acetate (10:1), giving 15.3 g of the desired product, mp 43°-45° C.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customthe solvents removed
  3. dissolutionthe residue dissolved in ether
  4. washwashed with water
  5. customdried
  6. customThis crude material was chromatographed on silica gel
  7. washeluting with hexane:ethyl acetate (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-3a5a2363e4984d999afdaf875d98fca9
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04762942

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