Oxygen → 2,8-Dimethyldibenzofuran

HRID 441757

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.O=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[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

Conditions

Temperature: 150 °C

Procedure

15 g of 4,4'-dimethyldiphenyl ether, 0.034 g (0.15 m. mole) of palladium acetate and 0.015 g (0.15 m. mole) of acetylacetone were placed in a glass vessel and this is placed in a 100 ml-autoclave. Then a mixture gas of nitrogen and oxygen of molar ratio 1:1 was filled in it to 50 kg/cm2 of inner pressure. The autoclave was shaken at 150° C. for 5 hours. After completion of the reaction, the reaction mixture was subjected to fractional distillation. After distilling out the unreacted 4,4'-dimethyldiphenyl ether, a distillate having b.p. 130°-135° C./12 mmHg was recrystallized from ethanol to give 2.6 g (13 m. moles) of 2,8-dimethyldibenzofuran. The obtained 2,8-dimethylbenzofuran showed m.p. 62°-64° C. (reference value, 64° C.).

Workup

customAfter completion of the reaction
distillationthe reaction mixture was subjected to fractional distillation
distillationAfter distilling out the unreacted 4,4'-dimethyldiphenyl ether
customwas recrystallized from ethanol

Sources & evidence

ORD record: ord-97e93d0900fa4ab98641e73a54e603f6
Source dataset: uspto-grants-1977_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04042603

Linked notes

Loading…