HCID 69205956, compound → HCID 69205784, compound

HRID 2378294Notes

Reaction equation

HRID 2378294 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27]CC)[CH:20]=2)=[O:18])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1C=CC=CC=1>C(O)C.[Pd]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([OH:27])[CH:20]=2)=[O:18])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[CH3:2]

Participants

4

Reactant 1

HCID 69205956HCID 69205956, compound

Product 1

HCID 69205784HCID 69205784, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (3-benzyloxy-4-methoxy-phenyl)-(3-ethoxy-4-methoxy-phenyl)-methanone (7.24 g), 20% palladium on charcol (0.22 g, 3% weight), and cyclohexcene (24 mL) in ethanol (48 mL) was refluxed overnight. The black suspension was filtered through a Celite pad, and the filtrate was evaporated to give (3-ethoxy-4-methoxy-phenyl)-(3-hydroxy-4-methoxy-phenyl)-methanone as an off-white solid (5.25 g, 94% yield): 1H NMR (DMSO-d6) δ 1.49 (t, J=7 Hz, 3H, CH2CH3), 3.95 (s, 3H, OCH3), 3.98 (s, 3H, OCH3), 4.16 (q, J=7 Hz, 2H, CH2CH3), 5.69 (s, 1H, OH), 6.87-6.93 (m, 2H, Ar), 7.35-7.43 (m, 4H, Ar). The product was used in the next step without further purification.

Workup

  1. temperaturewas refluxed overnight
  2. filtrationThe black suspension was filtered through a Celite pad
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-77bc52c409cd4ff28360ffc1fcb61f17
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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