1-Bromodecane → 4-(Decyloxy)-3-(1,1-dimethylethyl)benzoic acid methyl ester

HRID 1728892Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1728892
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(=O)([O-])[O-].[K+].[K+]>[I-].[K+].CC(=O)CC>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[C:6]([C:11]([CH3:12])([CH3:14])[CH3:13])[CH:5]=1

Komponenten

6

Edukt 3

HCID 81731-BromodecaneHCID 11430Potassium CarbonateHCID 13207060Methyl 3-tert-butyl-4-hydroxybenzoate

Produkt 1

HCID 539263074-(Decyloxy)-3-(1,1-dimethylethyl)benzoic acid methyl esterAusbeute 105,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 4875Potassium IodideKatalysatorHCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of 12.0 g of 3-(1,1-dimethylethyl)-4-hydroxybenzoic acid methyl ester, 11.15 g of 1-bromodecane, 9.95 g of potassium carbonate, 0.797 g of potassium iodide and 100 ml of 2-butanone is heated at reflux temperature for 40 hours. The reaction is cooled, filtered and the filtrate concentrated in vacuo. The residue is purified by chromatography (silica gel: 0-3% ethyl acetate/hexane) to give 18.49 g of the desired product as a light yellow oil.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux temperature for 40 hours
  3. temperatureThe reaction is cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe residue is purified by chromatography (silica gel: 0-3% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-7f11c824057a4b6ea25ba39b9a052d29
Quelldatensatz
uspto-grants-1994_07
Patentnummer
US05328921

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