2-(4-benzyloxy-phenoxy)-N-methyl-acetamide → 2-(4-hydroxyphenoxy)-N-methylacetamide

HRID 853148Notes

Reaction equation

HRID 853148 reaction equation
C([O:8][C:9]1[CH:20]=[CH:19][C:12]([O:13][CH2:14][C:15]([NH:17][CH3:18])=[O:16])=[CH:11][CH:10]=1)C1C=CC=CC=1>O1CCCC1.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][C:15]([NH:17][CH3:18])=[O:16])=[CH:19][CH:20]=1

Participants

4

Reactant 1

HCID 115436062-(4-benzyloxy-phenoxy)-N-methyl-acetamide

Product 1

HCID 181839132-(4-hydroxyphenoxy)-N-methylacetamideYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.7 g of 2-(4-benzyloxy-phenoxy)-N-methyl-acetamide [Example 2c)] in 150 ml of tetrahydrofurane was hydrogenated at atmospheric pressure and room temperature using 470 mg of palladium on charcoal (10%) as the catalyst. For the working-up, the reaction mixture was filtered over a Dicalite layer and the resulting solution was evaporated under reduced pressure. The residue was triturated in ether and the solid collected on a filter funnel. After drying there were obtained 2.95 g (93% of theory) of 2-(4-hydroxy-phenoxy)-N-methyl-acetamide as white crystals; MS: m/e=181 (M)+.

Workup

  1. customwas hydrogenated at atmospheric pressure and room temperature
  2. filtrationthe reaction mixture was filtered over a Dicalite layer
  3. customthe resulting solution was evaporated under reduced pressure
  4. customThe residue was triturated in ether
  5. customthe solid collected on a filter funnel
  6. customAfter drying there

Sources & evidence

ORD record
ord-e192a3bf20ed42e99777025f1c54e5a5
Source dataset
uspto-grants-2007_08
Patent number
US07253318B2

Reaction notes

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