HCID 131733003, compound → HCID 118184937, compound

HRID 2177396Notes

Reaction equation

HRID 2177396 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([O:10]CC2C=CC=CC=2)[CH:7]=[CH:6][C:5]=1/[CH:18]=[CH:19]/[C:20]([O:22][CH2:23][CH3:24])=[O:21])(=[O:3])[CH3:2].[H][H]>[Pd].C(OCC)(=O)C>[C:1]([C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:5]=1[CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 131733003HCID 131733003, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 118184937HCID 118184937, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
15 °C

Procedure

Into a 250-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed ethyl (2E)-3-[2-acetyl-4-(benzyloxy)phenyl]prop-2-enoate (1.09 g, 3.36 mmol, 1.00 equiv), ethyl acetate (30 mL), Palladium on carbon (700 mg), hydrogen was introduced last. The resulting solution was stirred overnight at 15° C. in an oil bath. The reaction progress was monitored by LCMS. The solids were removed by filtration and washed with EA. The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and the resulting mixture was concentrated under reduced pressure to give 0.8 g (96%) of ethyl 3-(2-acetyl-4-hydroxyphenyl)propanoate as a light yellow solid. Mass spectrum (ESI, m/z): Calcd. for C13H16O4, 235.1 (M−H). found 235.1.

Workup

  1. customInto a 250-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. additionwas introduced last
  4. customThe solids were removed by filtration
  5. washwashed with EA
  6. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationthe resulting mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-71e467b791504f9b9eb5f5292e96a5e6
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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