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1-Bromooctadecane → 3-Hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl ester

HRID 1757806
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1757806
[C:1]1([CH2:7][O:8][C:9](=[O:18])[C:10]2[CH:15]=[C:14]([OH:16])[CH:13]=[C:12]([OH:17])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[C:1]1([CH2:7][O:8][C:9](=[O:18])[C:10]2[CH:11]=[C:12]([O:17][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH3:20])[CH:13]=[C:14]([OH:16])[CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
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Komponenten

6

Edukt 3

HCID 82181-BromooctadecaneHCID 11430Potassium CarbonateHCID 112995373,5-Dihydroxybenzoic acid phenylmethyl ester

Produkt 1

HCID 152334763-Hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl esterAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittel
HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

A mixture of 30 g (0.123 mol) of 3,5-dihydroxybenzoic acid phenylmethyl ester, 40.9 g (0.123 mol) of 1-bromooctadecane, 17 g (0.123 mol) of anhydrous potassium carbonate in 500 ml of acetone and 10 ml of DMF was stirred at reflux for 25 hours. The reaction mixture was filtered and the filtrate was concentrated at reduced pressure to a solid. The residue was treated with water and the product was extracted with methylene chloride. The dried extract was concentrated at reduced pressure to a solid which was purified by HPLC using 1% ethyl acetate-methylene chloride to give 22 g (36% yield, mp 72°-75°) of 3-hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl ester. The structure was confirmed by nmr and mass spectra.

Aufarbeitung

  1. temperatureat reflux for 25 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated at reduced pressure to a solid
  4. additionThe residue was treated with water
  5. extractionthe product was extracted with methylene chloride
  6. extractionThe dried extract
  7. concentrationwas concentrated at reduced pressure to a solid which
  8. customwas purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-c447985c25864e36bbea96be0b94b5ab
Quelldatensatz
uspto-grants-1995_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05446189

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