HCID 21425193, compound → HCID 21425190, compound

HRID 258963Notes

Reaction equation

HRID 258963 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2(O)[CH2:12][CH:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH2:10]2)=[CH:5][CH:4]=1.[H][H]>[Pd].CCO>[CH3:20][O:19][C:16]1[CH:15]=[CH:14][C:13]([CH:11]2[CH2:12][CH:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[CH2:10]2)=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 21425193HCID 21425193, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21425190HCID 21425190, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1.3-bis(p-methoxyphenyl)cyclobutanol (13.2 g., 0.046 mole), 3.0 g. of 10% Pd/c, 1 ml. of 70% HClO4, and 100 ml. of 95% EtOH is shaken under 50 psi of H2 until hydrogen absorption is complete. The catalyst is removed by filtration and the filtrate is evaporated. A solution of the residue in ether is washed (5% Na HCO3, water) and dried (MgSO4). Evaporation of the ether yields a residue (11.4 g.) which is recrystallized (EtOH), affording 6.8 g. (55%) of the desired intermediate.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe filtrate is evaporated
  3. washA solution of the residue in ether is washed (5% Na HCO3, water)
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the ether
  6. customyields a residue (11.4 g.) which
  7. customis recrystallized (EtOH)
  8. customaffording 6.8 g

Sources & evidence

ORD record
ord-aca1f3182c4d48f8924312db893dd4a3
Source dataset
uspto-grants-1977_07
Patent number
US04035426

Reaction notes

Loading…