Tetrahydrofuran → 4-Octyloxy-benzoic acid 4-(4-hydroxy-cyclohexyl)-phenyl ester

HRID 2220009

Reaktionsgleichung

Reaktionsgleichung von HRID 2220009
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:6][C:5]=1O.C([O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=O)=[CH:32][CH:31]=1)CCCCCCC.[CH3:39][CH:40](C)N=C=NC(C)C.[CH2:48]1COC[CH2:49]1>CN(C1C=CN=CC=1)C>[OH:29][CH:30]1[CH2:31][CH2:32][CH:33]([C:34]2[CH:49]=[CH:48][C:1]([O:2][C:3](=[O:20])[C:4]3[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:6][CH:5]=3)=[CH:40][CH:39]=2)[CH2:37][CH2:38]1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 12734DiisopropylcarbodiimideHCID 172314-(Octyloxy)benzoic acidHCID 11536459Methyl 2-hydroxy-4-octyloxybenzoate

Produkt 1

HCID 693073454-Octyloxy-benzoic acid 4-(4-hydroxy-cyclohexyl)-phenyl esterAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 142844-(Dimethylamino)pyridineKatalysator

Versuchsvorschrift

10 g (0.052 mol) of 4-(4-Hydroxy-cyclohexyl)-phenol obtained in Step 1 of the synthesis of the compound 27 and 13.02 g (0.052 mol) of 4-Octyloxy-benzoic acid are dissolved in 120 mL of anhydrous THF. 0.65 g (0.0052 mol) of DMAP, then 6.56 g (0.052 mol) of DIC are added. The mixture is stirred at room temperature overnight. The solvent is distilled off and then the resulting product is purified by column chromatography on silica gel using mixture of hexane and ethyl acetate (70:30) as eluent and recrystallised from ethanol to give a pure product as a white solid (6 g, 27% yield).

Aufarbeitung

  1. distillationThe solvent is distilled off
  2. customthe resulting product is purified by column chromatography on silica gel using mixture of hexane and ethyl acetate (70:30) as eluent
  3. customrecrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-6785549646bf4f4087b04dfa766f68f1
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07416682B2

Verknüpfte Notizen

Wird geladen…