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Methyl iodide → 3-[[6-(2,3-Dihydroxyphenyl)hexyl]oxy]-5-(octadecyloxy)benzoic acid methyl ester

HRID 1492867
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1492867
[OH:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH:24]=1)[C:19]([OH:21])=[O:20].[C:44](=O)(O)[O-].[Na+].CI>CN(C=O)C>[CH3:44][O:20][C:19](=[O:21])[C:18]1[CH:22]=[C:23]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH:24]=[C:16]([O:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([OH:8])[C:2]=2[OH:1])[CH:17]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6328Methyl iodide2×HCID 516892Sodium Bicarbonate2×HCID 98516283-[[6-(2,3-Dihydroxyphenyl) hexyl]oxy]-5-(octadecyloxy)benzoic acid

Produkt 1

HCID 542033863-[[6-(2,3-Dihydroxyphenyl)hexyl]oxy]-5-(octadecyloxy)benzoic acid methyl esterAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

A mixture of 0.15 g (0.25 mmol) of 3-[[6-(2,3-dihydroxyphenyl) hexyl]oxy]-5-(octadecyloxy)benzoic acid, 0.05 g (0.6 mmol) of sodium bicarbonate and 0.64 ml (10 mmol) of methyl iodide in 3 ml of DMF was stirred and heated at 40° for 5 days. An additional 0.32 ml of methyl iodide and 0.05 g of sodium bicarbonate were added and heating at 40° was continued for 6 days. The solvent was removed at reduced pressure, the residue was extracted with ethyl acetate and the extract was washed with water. The dried extract was concentrated to an oil which was purified by chromatography on 4 g of silica gel using 25% ethyl acetate-hexane to give 0.104 g (68% yield, mp 82°-84°) of 3-[[6-(2,3-dihydroxyphenyl)hexyl]oxy]-5-(octadecyloxy)benzoic acid methyl ester.

Aufarbeitung

  1. temperatureheated at 40° for 5 days
  2. temperatureheating at 40°
  3. customThe solvent was removed at reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washthe extract was washed with water
  6. extractionThe dried extract
  7. concentrationwas concentrated to an oil which
  8. customwas purified by chromatography on 4 g of silica gel using 25% ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-300fba6623d8429b84a1c8fb19549d50
Quelldatensatz
uspto-grants-1994_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05374772

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