Methyl 3-(4-(benzyloxy)phenyl)-3-oxopropanoate → Methyl (4-Hydroxybenzoyl)acetate

HRID 922324Notes

Reaction equation

HRID 922324 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:21])[CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>[C].[Pd].C(OCC)(=O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15](=[O:21])[CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 58806802Methyl 3-(4-(benzyloxy)phenyl)-3-oxopropanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 508465Methyl (4-Hydroxybenzoyl)acetateYield 98.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a 50 mL RB flask fitted with magnetic stirrer were charged ethyl acetate (15 mL), to that stirred solvent was added methyl 3-[4-(benzyloxy)phenyl]-3-oxopropanoate (0.3 g, 1.05 mmol), and palladium carbon 10% (80 mg) was added. After addition, the hydrogen balloon was fixed to the reaction mixture and stirred at room temperature for 1 h. After 3 h, the reaction mixture was filtered through celite. Then the organic layer was concentrated and dried. The product was obtained as colourless liquid (0.2 g, Yield: 98%).

Workup

  1. customTo a 50 mL RB flask fitted with magnetic stirrer
  2. additionwas added
  3. additionAfter addition
  4. stirringstirred at room temperature for 1 h
  5. filtrationthe reaction mixture was filtered through celite
  6. concentrationThen the organic layer was concentrated
  7. customdried

Sources & evidence

ORD record
ord-22e8eafd66604a16adc4842b12db5e8e
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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