Hydrochloric Acid → HCID 178458878, Verbindung

HRID 1084666Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1084666
[C:1]([C:5]1[C:6](=[O:31])[CH2:7][CH:8]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:19][CH:18]=2)[CH:9](C(OCC)=O)[C:10]=1[OH:11])(=[O:4])[CH2:2][CH3:3].[OH-].[Na+].Cl>C(O)C.O>[C:1]([C:5]1[C:6](=[O:31])[CH2:7][CH:8]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[CH:19][CH:18]=2)[CH2:9][C:10]=1[OH:11])(=[O:4])[CH2:2][CH3:3]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 200622872-Propionyl-3-hydroxy-5-(4-benzyloxyphenyl)-4-(carboethoxy)cyclohex-2-en-1-one

Produkt 1

HCID 178458878HCID 178458878, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 54 g (0.13 mol) of 2-propionyl-3-hydroxy-5-(4-benzyloxyphenyl)-4-(carboethoxy)cyclohex-2-en-1-one 30 g (0.37 mol)of 50 percent sodium hydroxide in 450 mL of 95 percent ethanol and 100 mL of water was stirred mechanically and heated at about 70° C. for 16 hours. The resulting clear yellow solution was cooled to about 60° C. and treated with 50 mL of concentrated HCl (some material was lost as the ensuing decarboxylation reaction erupted from the reaction vessel). The product precipitated from the solution and was isolated by filtration. Recrystallization from absolute ethanol gave the above named product as a beige crystalline solid in a yield of 24 g (54 percent of theoretical). The product melted at 114°-115° C.: 1H NMR (CDCl3) δ1.17 (t, 3H, --CH3), 2.60-3.48 (m, 7H, ring protons and --CH2CH3), 5.05 (s, 2H, ArCH2O--), 6.83-7.55 (m, 9H, ArH's), 18.1 (s, 1H, enol, H).

Aufarbeitung

  1. temperatureThe resulting clear yellow solution was cooled to about 60° C.
  2. customwas lost as the ensuing decarboxylation reaction
  3. customThe product precipitated from the solution
  4. customwas isolated by filtration
  5. customRecrystallization from absolute ethanol
  6. customgave the

Quellen und Nachweise

ORD-Eintrag
ord-414671d6be0e4253980c0a9fcd8d3d53
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05006159

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