Water → n-Octadecyl 4-tert.-butyl-2,6-dimethyl-3-hydroxyphenylacetate

HRID 838865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 838865
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([CH2:12][C:13]([OH:15])=[O:14])=[C:7]([CH3:16])[C:6]=1[OH:17])([CH3:4])([CH3:3])[CH3:2].[CH2:18](O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([CH2:12][C:13]([O:15][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH3:18])=[O:14])=[C:7]([CH3:16])[C:6]=1[OH:17])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8221Stearyl AlcoholHCID 521998p-Toluenesulfonic acid monohydrateHCID 203459052-(4-tert-Butyl-3-hydroxy-2,6-dimethylphenyl)acetic acid

Produkt 1

HCID 20345920n-Octadecyl 4-tert.-butyl-2,6-dimethyl-3-hydroxyphenylacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

10.68 grams of the compound of Example 5, 11.4 grams of n-octadecanol and 0.8 grams of p-toluene sulfonic acid monohydrate were dispersed in 150 ml of toluene and heated at reflux for seven hours during which the water collected by azeotropic distillation was almost equal to the theory. The reaction mixture was successively washed with water, aqueous saturated sodium bicarbonate solution, and then with water once again until the wash water was neutral. After drying over anhydrous sodium sulfate and filtering free of the drying agent, the clear filtrate was evaporated at reduced pressures to yield the desired product as residue. After successive crystallizations from acetonitrile and n-heptane, the desired compound was isolated as white crystals melting at 57° to 59° C (Compound 1).

Aufarbeitung

  1. temperatureheated
  2. distillationcollected by azeotropic distillation
  3. washThe reaction mixture was successively washed with water, aqueous saturated sodium bicarbonate solution
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. filtrationfiltering free of the drying agent
  6. customthe clear filtrate was evaporated at reduced pressures

Quellen und Nachweise

ORD-Eintrag
ord-6635f45b5745449a94716de8c0ee17c0
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04093618

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