Ethyl 2-bromoheptanoate → alpha-[p-(1-Cyclooctenyl)-phenoxy]-heptanoic acid ethyl ester

HRID 1764127

Reaktionsgleichung

Reaktionsgleichung von HRID 1764127
[Na].[C:2]1([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=1.[CH2:17]([O:19][C:20](=[O:28])[CH:21](Br)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH3:18]>C(O)C>[CH2:17]([O:19][C:20](=[O:28])[CH:21]([O:16][C:13]1[CH:12]=[CH:11][C:10]([C:2]2[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=2)=[CH:15][CH:14]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH3:18]

Komponenten

5

Edukt 3

HCID 95333Ethyl 2-bromoheptanoateHCID 5360545SodiumHCID 53964233p-(1-Cyclooctenyl)-phenol

Produkt 1

HCID 54549182alpha-[p-(1-Cyclooctenyl)-phenoxy]-heptanoic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To 2.1 g of sodium in 180 ml of absolute ethanol are added with stirring 15.0 g of p-(1-cyclooctenyl)-phenol. After stirring has continued for a further 30 minutes, 28.5 g of 2-bromo-heptanoic acid ethyl ester are slowly added dropwise to this solution and the mixture is maintained at 50° C for 24 hours. Upon removal of the solvent in vacuo, the residue is partitioned at 0° C between ether and 2N sodium hydroxide solution. The organic phase is washed until neutral, dried over sodium sulphate and evaporated in vacuo, to yield the oily α-[p-(1-cyclooctenyl)-phenoxy]-heptanoic acid ethyl ester of the formula ##STR7##

Aufarbeitung

  1. customUpon removal of the solvent in vacuo
  2. customthe residue is partitioned at 0° C between ether and 2N sodium hydroxide solution
  3. washThe organic phase is washed until neutral,
  4. dry with materialdried over sodium sulphate
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-01cda1a183b2486eab5600e637d4d1ba
Quelldatensatz
uspto-grants-1978_09
Patentnummer
US04115416

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