Phenol, p-(1-cyclohexen-1-yl)- → alpha-[p-(1-Cyclohexenyl)-phenoxy]-undecanoic acid ethyl ester

HRID 1764139

Reaktionsgleichung

Reaktionsgleichung von HRID 1764139
[Na].[C:2]1([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=1.[CH2:15]([O:17][C:18](=[O:30])[CH:19](Br)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH3:16]>C(O)C>[CH2:15]([O:17][C:18](=[O:30])[CH:19]([O:14][C:11]1[CH:10]=[CH:9][C:8]([C:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=2)=[CH:13][CH:12]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH3:16]

Komponenten

5

Edukt 3

HCID 69727Phenol, p-(1-cyclohexen-1-yl)-HCID 95582Ethyl 2-bromoundecanoateHCID 5360545Sodium

Produkt 1

HCID 53857244alpha-[p-(1-Cyclohexenyl)-phenoxy]-undecanoic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel3×

Versuchsvorschrift

To a solution of 1.6 g of sodium in 100 ml of absolute ethanol, 10 g of p-(1-cyclohexenyl)-phenol in a small amount of absolute ethanol are added at room temperature under anhydrous conditions and with stirring. 25.2 Grams of α-bromo-undecanoic acid ethyl ester are then added dropwise. and the reaction mixture is stirred for 24 hours at 50° C. The ethanol is subsequently stripped off in vacuo and the residue is partitioned between water and ice-cold N solution hydroxide solution. The organic phase is washed until neutral, dried over sodium sulphate and concentrated in vacuo. The residue yields the crude α-[p-(1-cyclohexenyl)-phenoxy]-undecanoic acid ethyl ester of the formula ##STR19## in the form of an oil.

Aufarbeitung

  1. stirringand the reaction mixture is stirred for 24 hours at 50° C
  2. customthe residue is partitioned between water and ice-cold N solution hydroxide solution
  3. washThe organic phase is washed until neutral,
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d3d3d7cfd2774f5094e2fc5c3ec16fae
Quelldatensatz
uspto-grants-1978_09
Patentnummer
US04115416

Verknüpfte Notizen

Wird geladen…