Ethyl 3-(4-methoxyphenyl)-2-methylpropanoate → 6-Methoxy-2-methyl-2,3-dihydro-1H-inden-1-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([CH3:16])[C:11]([O:13]CC)=O)=[CH:5][CH:4]=1>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6]([CH2:9][CH:10]([CH3:16])[C:11]2=[O:13])=[CH:7][CH:8]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Ethyl β-(p-methoxyphenyl)-α-methylpropionate is added to 56 g of polyphosphoric acid with stirring at 50°C. The mixture is then heated to 83°-90°C for 2 hours. The cooled reaction mixture is poured slowly into a mixture of water and crushed ice with stirring and extracted with 3 × 300 ml of ether. The etheral solution is washed with 10% sodium bicarbonate solution followed by cold water to neutral, then with saturated sodium chloride solution and dried over magnesium sulfate for 1.5 hours and filtered. The solvent is removed on an evaporator and the residue distilled to obtain 6-methoxy-2-methylindanone.
Workup
- temperatureThe mixture is then heated to 83°-90°C for 2 hours
- customThe cooled reaction mixture
- customcrushed ice
- stirringwith stirring
- extractionextracted with 3 × 300 ml of ether
- washThe etheral solution is washed with 10% sodium bicarbonate solution
- dry with materialdried over magnesium sulfate for 1.5 hours
- filtrationfiltered
- customThe solvent is removed on an evaporator
- distillationthe residue distilled
Sources & evidence
- ORD record
- ord-8b8dc9d019cc431599a2ae4130e285d9
- Source dataset
- uspto-grants-1976_09
- Patent number
- US03983253
Reaction notes
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