4-Acetoxy-3-phenyl-butyric Acid Methyl Ester → Dihydro-4-phenylfuran-2(3H)-one
Reaction equation
COC(=O)C[CH:5]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:6][O:7][C:8](=[O:10])[CH3:9]>O1CCOCC1.S(=O)(=O)(O)O>[C:11]1([CH:5]2[CH2:6][O:7][C:8](=[O:10])[CH2:9]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 45 °C
Procedure
A solution of 4-acetoxy-3-phenyl-butyric acid methyl ester, (4.5 g, 19.2 mmol) in 1,4-dioxane (29 mL) and sulfuric acid (29 mL) is stirred at room temperature for one hour then heated at 45° C. for 18 h. Volatile solvents are evaporated and the residue is extracted with toluene. The combined organic extracts are extracted with water and brine, filtered, and concentrated to yield the title compound, 2.2 g (71%), as a colorless liquid.
Workup
- customVolatile solvents are evaporated
- extractionthe residue is extracted with toluene
- extractionThe combined organic extracts are extracted with water and brine
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c72e25f5b65a41dcba6135476c5cb717
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07087626B2
Reaction notes
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