HCID 11299135, compound → Ethyl 2-phenylbenzoate

HRID 1251032Notes

Reaction equation

HRID 1251032 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH2:10][CH2:9][C:8]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C.O.[Pd]>[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 1

HCID 11299135HCID 11299135, compound

Product 1

HCID 9920952Ethyl 2-phenylbenzoateYield 80%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl 2-phenylcyclohexa-1,3-dienecarboxylate(90 mg, 0.395 mmol) and 5% Pd/C(50 mg) in acetic acid(1.5 ml) and water(1.5 ml) was refluxed for 2hr. The reaction mixture was filtrated and the solvent was evaporated under reduced pressure. Toluene was added to the residue and it was dried over MgSO4. After removal of the solvent, the residue was purified by column chromatography on silica gel with n-hexane-AcOEt to afford 71 mg of ethyl 2-phenylbenzoate(y=80.0%) as a pale yellow oil. 1H-NMR(ppm, 300 MHz, CDCl3) δ 7.82(1H, dd, J=1.4 and 7.7 Hz), 7.10-7.60(8H), 4.08(2H, d, J=7.0 Hz), 0.98(3H, t, J=7.0 Hz).

Workup

  1. temperaturewas refluxed for 2hr
  2. filtrationThe reaction mixture was filtrated
  3. customthe solvent was evaporated under reduced pressure
  4. additionToluene was added to the residue and it
  5. dry with materialwas dried over MgSO4
  6. customAfter removal of the solvent
  7. customthe residue was purified by column chromatography on silica gel with n-hexane-AcOEt

Sources & evidence

ORD record
ord-fe10ca4e28184e188aa8531a9a38f3e5
Source dataset
uspto-grants-2002_01
Patent number
US06340772B1

Reaction notes

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