Toluene → 3-(3,5-Di-t-butyl-4-hydroxyphenyl)-propionic acid allyl ester

HRID 2059123

Reaktionsgleichung

Reaktionsgleichung von HRID 2059123
[NH2-].[Li+].[CH2:3]([OH:6])[CH:4]=[CH2:5].C[O:8][C:9](=O)[CH2:10][CH2:11][C:12]1[CH:17]=[C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:15]([OH:22])=[C:14]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:13]=1.C1(C)C=CC=CC=1>C(O)(=O)C>[CH2:3]([O:6][C:9](=[O:8])[CH2:10][CH2:11][C:12]1[CH:17]=[C:16]([C:18]([CH3:19])([CH3:21])[CH3:20])[C:15]([OH:22])=[C:14]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:13]=1)[CH:4]=[CH2:5]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 7858Allyl AlcoholHCID 24532Lithium amideHCID 62603Methyl di-t-butyl hydroxyhydrocinnamate

Produkt 1

HCID 205457203-(3,5-Di-t-butyl-4-hydroxyphenyl)-propionic acid allyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

0.2 g of lithium amide and in the course of 5 hours 38 g of allyl alcohol are added at 150° C. under nitrogen to 146 g of 3-(3,5-di-t-butyl-4-hydroxyphenyl)-propionic acid methyl ester. After completion of the addition, stirring is maintained at 150° C. for a further 10 hours. The brownish reaction mixture is cooled to about 100° C., and 150 ml of toluene, 0.5 g of concentrated acetic acid and 10 g of "Celite Hyflow Supercel" (product of Johns Manville Corp., USA) are added. There is thus obtained, after filtration and then removal of the solvent in vacuo, the title compound in crystalline form, m.p. about 40° C.

Aufarbeitung

  1. additionAfter completion of the addition
  2. customThe brownish reaction mixture
  3. temperatureis cooled to about 100° C.
  4. customThere is thus obtained
  5. filtrationafter filtration
  6. customremoval of the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-504d49677280405fba3127a71044c487
Quelldatensatz
uspto-grants-1982_03
Patentnummer
US04322303

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