Ethanol → HCID 22151967, compound

HRID 1111287Notes

Reaction equation

HRID 1111287 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:13](=O)[C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[O:10][CH:9]([C:19]([O:21][CH3:22])=[O:20])[O:8][C:7]=2[CH:23]=1.C(O)C.C(OCC)(=O)C.[H][H]>[Pd].C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:13][C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[O:10][CH:9]([C:19]([O:21][CH3:22])=[O:20])[O:8][C:7]=2[CH:23]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 22151956HCID 22151956, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22151967HCID 22151967, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Methyl 3-methoxy-12H-dibenzo[d,g][1,3]-dioxocin-12-one-6-carboxylate (1.35 g, 4.3 mmol) was combined with 35 ml of ethanol, 15 ml of ethyl acetate, 6 ml of acetic acid, and 0.70 g of 5 percent palladium on carbon catalyst and the suspension was placed on a Parr hydrogenator under 50 psi of hydrogen for 18 hours. The catalyst was removed by filtration and the filtrate was diluted with 300 ml of ether and 100 ml of water and the layers separated. The organic layer was extracted with 3-100 ml portions of water and 2-100 ml portions of saturated aqueous sodium bicarbonate and was then dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure. The residue was purified by preparative liquid chromatography on silica gel eluting with a 15:85 mixture of ether and hexane to obtain 0.76 g (59 percent of theory) of the title compound as a white powder melting at 93°-95° C. The proton nmr spectrum was consistent with the assigned structure.

Workup

  1. customThe catalyst was removed by filtration
  2. additionthe filtrate was diluted with 300 ml of ether and 100 ml of water
  3. customthe layers separated
  4. extractionThe organic layer was extracted with 3-100 ml portions of water and 2-100 ml portions of saturated aqueous sodium bicarbonate
  5. dry with materialwas then dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customThe residue was purified by preparative liquid chromatography on silica gel eluting with a 15:85 mixture of ether and hexane

Sources & evidence

ORD record
ord-b322bd410de044b0819b46596cefc149
Source dataset
uspto-grants-1990_12
Patent number
US04979978

Reaction notes

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