3-Hydroxybenzoic Acid → HCID 15225618, Verbindung

HRID 1770128Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1770128
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH:11]1([CH:17]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O.O1CCOCC1>[CH:11]1([CH:17]([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[O:1][C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=2)[C:5]([OH:7])=[O:6])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Komponenten

7

Edukt 4

HCID 74203-Hydroxybenzoic AcidHCID 11776TriphenylphosphineHCID 78197alpha-CyclohexylcyclohexanemethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Produkt 1

HCID 15225618HCID 15225618, VerbindungAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 3-hydroxybenzoic acid (1.61 g, 8.2 mmol), dicyclohexylmethanol (1.61 g, 8.2 mmol), triphenylphosphine (2.05 g, 7.82 mmol) and dioxane (35 ml) was added diethyl azodicarboxylate (1.41 ml, 8.94 mmol), and the resultant mixture was refluxed for 3 days. The reaction mixture was allowed to warm up to room temperature, poured into chilled water and extracted with diethyl ether. The organic layer was concentrated, and the residue was dissolved in a mixture of methanol (20 ml), tetrahydrofuran (6.5 ml) and water (2.0 ml), mixed with potassium hydroxide (1.16 g) and stirred for 2 hours. The mixture was poured into chilled water, acidified, and extracted with ethyl acetate. The organic layer was concentrated, and the resultant residue was recrystallized from hexane to give the titled compound (0.43 g, yield 18%).

Aufarbeitung

  1. additionpoured
  2. extractionextracted with diethyl ether
  3. concentrationThe organic layer was concentrated
  4. dissolutionthe residue was dissolved in a mixture of methanol (20 ml), tetrahydrofuran (6.5 ml) and water (2.0 ml)
  5. additionmixed with potassium hydroxide (1.16 g)
  6. additionThe mixture was poured
  7. temperatureinto chilled water
  8. extractionextracted with ethyl acetate
  9. concentrationThe organic layer was concentrated
  10. customthe resultant residue was recrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-d90969d5d77d4293bc01a73a9a256904
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05385917

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