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

HRID 2248384Notes

Reaction equation

[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

Participants

Conditions

Temperature: 70 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-9b0aae62217b41c7b328aa2ef758ebcc
Source dataset: uspto-grants-1991_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05039691

Reaction notes

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