Ethyl 2-(4-benzyloxyphenyl)-2-methylpropanoate → Ethyl 2-(4-hydroxyphenyl)-2-methylpropanoate

HRID 524409Notes

Reaction equation

HRID 524409 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:22])([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][CH:10]=1)C1C=CC=CC=1>O.[Pd].C(OCC)(=O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([CH3:21])([CH3:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:13][CH:14]=1

Participants

5

Reactant 1

HCID 69644592Ethyl 2-(4-benzyloxyphenyl)-2-methylpropanoate

Product 1

HCID 21269145Ethyl 2-(4-hydroxyphenyl)-2-methylpropanoateYield 62.1%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Under inert atmosphere, a round bottom flask was charged with ethyl 2-(4-benzyloxyphenyl)-2-methyl-propanoate (15 g, mmol) and ethyl acetate (200 mL). To above reaction mixture 2-3 drops of water was added followed by Pd/C. Reaction mixture allowed to stir and evacuated the flask until solvent begins to bubble and then carefully backfill with nitrogen gas (repeated twice). Nitrogen balloon was replaced by hydrogen bladder and flask was again evacuated and refilled with hydrogen (repeated twice). The reaction mixture thus maintained under hydrogen atmosphere was allowed to stir overnight at room temperature. The reaction mixture was filtered through cellite pad and the filtrate was concentrated under reduced pressure to afford 6.5 g of product.

Workup

  1. additionwas added
  2. customReaction mixture
  3. customevacuated the flask until solvent
  4. customto bubble
  5. customwas again evacuated
  6. additionrefilled with hydrogen (
  7. temperatureThe reaction mixture thus maintained under hydrogen atmosphere
  8. stirringto stir overnight at room temperature
  9. filtrationThe reaction mixture was filtered through cellite pad
  10. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fdde32cfae14428f87c38f5a138ff54c
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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