Triethylamine → 3-(4-Methoxyphenyl)cyclobutan-1-one

HRID 1578802Notes

Reaction equation

HRID 1578802 reaction equation
Cl[C:2]1[C:3](=[O:14])[CH2:4][C:5]=1[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1.C(N(CC)CC)C>[Pd].CO>[CH3:13][O:12][C:9]1[CH:8]=[CH:7][C:6]([CH:5]2[CH2:4][C:3](=[O:14])[CH2:2]2)=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 214251912-Chloro-3-(p-methoxyphenyl)-2-cyclobuten-1-one

Product 1

HCID 114466413-(4-Methoxyphenyl)cyclobutan-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Chloro-3-(p-methoxyphenyl)-2-cyclobuten-1-one (17.4 g., 0.084 mole), triethylamine (11.7 ml., 0.084 mole), and 2.1 g. of 10% Pd/C in 300 ml. of 10% aqueous methanol is shaken under H2 (50 psi) until reduction is complete (30 min). The mixture is filtered and the filtrate evaporated. An ether solution of the residue is washed (water), dried (MgSO4), and evaporated to give 15.4 g. of an oil which is chromatographed on alumina using benzene.

Workup

  1. custom(30 min)
  2. filtrationThe mixture is filtered
  3. customthe filtrate evaporated
  4. washAn ether solution of the residue is washed (water)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give 15.4 g
  8. customof an oil which is chromatographed on alumina

Sources & evidence

ORD record
ord-71cca5fb87c54723ba72c4103f608580
Source dataset
uspto-grants-1976_02
Patent number
US03939196

Reaction notes

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