1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethanone → HCID 15329251, compound

HRID 424027Notes

Reaction equation

HRID 424027 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[O:21])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[H][H]>[Pd].CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([OH:21])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

5

Reactant 2

HCID 6418291-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 15329251HCID 15329251, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

160 ml of methanol, 32.6 g of recrystallized 1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethanone prepared according to Example 4 (114 mmol) and 3.25 g of 5% Pd/C of JM type 87 L are introduced into a hydrogenation reactor and hydrogen is introduced under a pressure of 5 to 6 bar at ambient temperature for 10 h. The catalyst is filtered off at 40° C. and the temperature is brought back to ambient temperature in order to recover 29 g of 1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethanol, i.e. a yield of 88.4% with respect to the starting ketone, which exhibits a melting point of 101-102° C.

Workup

  1. additionare introduced into a hydrogenation reactor
  2. filtrationThe catalyst is filtered off at 40° C.
  3. customis brought back to ambient temperature in order
  4. customto recover 29 g of 1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethanol, i.e. a yield of 88.4% with respect to the starting ketone, which

Sources & evidence

ORD record
ord-19965d345d2c445ba877cb30f9ce42e4
Source dataset
uspto-grants-2012_01
Patent number
US08101804B2

Reaction notes

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