Hydrogen Peroxide → 2(3H)-Furanone, dihydro-5-(hydroxymethyl)-3,3-diphenyl-

HRID 2248384Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2248384
[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([CH2:11][CH:12]=[CH2:13])[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:20]O>C(O)=O>[OH:20][CH2:13][CH:12]1[O:9][C:8](=[O:10])[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:11]1

Komponenten

4

Edukt 2

HCID 784Hydrogen PeroxideHCID 2272562,2-Diphenylpent-4-enoic acid

Produkt 1

HCID 99702452(3H)-Furanone, dihydro-5-(hydroxymethyl)-3,3-diphenyl-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

2,2-Diphenyl-4-pentenoic acid (5.0 g, 20 mmol.), 20 mL of formic acid and 2.4 mL (22 mmol.) of 30% hydrogen peroxide were stirred at 70° C. for 25 hours at ambient temperature. The solvents were evaporated at reduced pressure, the residue taken up in 20 mL of methanol and a solution of 750 mg solid NaOH in 10 mL of water was added. The mixture was warmed at 70° C. to solution, about 1 hour before cooling and acidifying with 6N hydrochloric acid. The product was extracted with ether, the organics dried (MgSO4) and evaporated at reduced pressure to give an oil in quantitative yield, the H NMR indicated a clean reaction product which was carried on without further purification. Analytical TLC (silica, 9:1, methylene chloride: EtAc) R.function. 0.35; IR (neat) 3419, 3060, 2936, 1763, 1177, 786, 763, 699 cm-1 ; 1H NMR (CDCl3)δ 2.5-2.65 (bs, 1H), 2.84-3.02 (m, 2H), 3.64-3.72 (m, 1H), 3.92-4.00 (m, 1H), 4.41-4.51 (m, 1H), 7.2-7.4 (m, 10H).

Aufarbeitung

  1. customThe solvents were evaporated at reduced pressure
  2. additiona solution of 750 mg solid NaOH in 10 mL of water was added
  3. temperaturebefore cooling
  4. extractionThe product was extracted with ether
  5. dry with materialthe organics dried (MgSO4)
  6. customevaporated at reduced pressure
  7. customto give an oil in quantitative yield
  8. customwas carried on without further purification

Quellen und Nachweise

ORD-Eintrag
ord-9b0aae62217b41c7b328aa2ef758ebcc
Quelldatensatz
uspto-grants-1991_08
Patentnummer
US05039691

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