3,6-Dimethyl-5,6-dihydro-1-benzofuran-2(4H)-one → 3,6-Dimethyl-1-benzofuran-2(3H)-one
Reaction equation
[CH3:1][C:2]1[C:3](=[O:12])[O:4][C:5]2[C:6]=1[CH2:7][CH2:8][CH:9]([CH3:11])[CH:10]=2>[Pd].C(OCCCC)(=O)/C=C\C(OCCCC)=O>[CH3:1][CH:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:5]=2[O:4][C:3]1=[O:12]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 170 °C
Procedure
A mixture of 1000 g of 5,6-dihydro-3,6-dimethyl-2(4H)-benzofuranone, 2000 ml of dibutyl maleate and 50 g of palladium-on-charcoal, 5% by weight, was heated for approx. 3 hours at 170° C. in an autoclave under autogenous pressure. After filtration, the product was purified by fractionating on an 80 cm packed column. Approx. 735 g of pure 3,6-dimethyl-2(3H)-benzofuranone were obtained at a b.p. of approx. 90° C. at 1 mbar.
Workup
- filtrationAfter filtration
- customthe product was purified
Sources & evidence
- ORD record
- ord-1fd7073ebc1c46d998433751bed8ae28
- Source dataset
- uspto-grants-2002_05
- Patent number
- US06391365B1
Reaction notes
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