Ethylene glycol diacetate → 2,8-Dimethyldibenzofuran

HRID 441759

Reaction equation

HRID 441759 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.C(CC(=O)C)(=O)C.C(OCCOC(=O)C)(=O)C>C([O-])(=O)CC.[Pd+2].C([O-])(=O)CC>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:8][C:9]3[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=3[C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 8121Ethylene glycol diacetateHCID 31261AcetylacetoneHCID 74098Benzene, 1,1'-oxybis[4-methyl-

Product 1

HCID 6393192,8-DimethyldibenzofuranYield 18.7%

Reagents, catalysts & solvents 1

HCID 11459426Palladium(II) propionateCatalyst

Procedure

This example was carried out under the same conditions as in Example 1 except that 15.0 g of 4,4'-dimethyldiphenyl ether, 0.038 g (0.15 m. mole) of palladium propionate, 0.015 g (0.15 m. mole) of acetylacetone and 5 ml of ethylene glycol diacetate were employed. As a result, 2.78 g (14 m. moles) of 2,8-dimethyldibenzofuran and 0.78 g (2.0 m. moles) of the dimer also obtained.

Sources & evidence

ORD record
ord-bbfe23b2dffb41458a1fb8767edbb62f
Source dataset
uspto-grants-1977_08
Patent number
US04042603

Linked notes

Loading…