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1-Octyloxy-2,2,6,6-tetramethylpiperidin-4-ol → HCID 19831354, Verbindung

HRID 1493415
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1493415
[C:1]([C:9]1[CH:20]=[CH:19][C:12]([O:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:11][C:10]=1[OH:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OC1[CH2:28][C:27]([CH3:30])([CH3:29])[N:26]([O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:25]([CH3:41])([CH3:40])[CH2:24]1>C1(C)C(C)=CC=CC=1>[OH:21][C:10]1[CH:11]=[C:12]([O:13][CH2:14][C:15]([O:17][CH:18]2[CH2:30][C:27]([CH3:28])([CH3:29])[N:26]([O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:25]([CH3:40])([CH3:41])[CH2:24]2)=[O:16])[CH:19]=[CH:20][C:9]=1[C:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:8]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 113466831-Octyloxy-2,2,6,6-tetramethylpiperidin-4-olHCID 14618907Methyl 4-Benzoyl-3-hydroxyphenoxyacetate

Produkt 1

HCID 19831354HCID 19831354, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 22.0 g (76.8 mmol) of methyl 4-benzoyl-3-hydroxyphenoxyacetate, 32.9 g (0.115 mol) of 4-hydroxy-1-octyloxy-2,2,6,6-tetramethylpiperidine, and 100 ml of xylene is heated at reflux. Water is removed by fractional distillation. The reaction mixture is cooled to 80° C., treated with 2.1 g of lithium amide, and diluted with 50 ml of xylene. The reaction mixture is heated at reflux for 2 hours, and methanol is removed by fractional distillation. The reaction mixture is cooled, then diluted with diethyl ether (250 ml). The organic solution is washed with 1N hydrochloric acid (200 ml), and solids are removed by filtration. The solution is washed with saturated sodium bicarbonate solution (100 ml), dried over magnesium sulfate, and concentrated to an oil. Purification by flash chromatography on silica gel (85:15 heptane: ethyl acetate) affords 32.6 g (79% yield) of the title compound, a yellow syrup.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux
  3. customWater is removed by fractional distillation
  4. additiontreated with 2.1 g of lithium amide
  5. additiondiluted with 50 ml of xylene
  6. temperatureThe reaction mixture is heated
  7. temperatureat reflux for 2 hours
  8. custommethanol is removed by fractional distillation
  9. temperatureThe reaction mixture is cooled
  10. additiondiluted with diethyl ether (250 ml)
  11. washThe organic solution is washed with 1N hydrochloric acid (200 ml), and solids
  12. customare removed by filtration
  13. washThe solution is washed with saturated sodium bicarbonate solution (100 ml)
  14. dry with materialdried over magnesium sulfate
  15. concentrationconcentrated to an oil
  16. customPurification by flash chromatography on silica gel (85:15 heptane: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c6c849ec003b4166905c300bee58cc1e
Quelldatensatz
uspto-grants-1991_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05021478

Notizen zur Reaktion

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