4-Coumaric acid → 3-(4-Hydroxyphenyl)propionic acid

HRID 1178068Notes

Reaction equation

HRID 1178068 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[H][H]>CO.[Pd]>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 3224-Coumaric acidHCID 178418361HCID 178418361, compound2×

Product 1

HCID 103943-(4-Hydroxyphenyl)propionic acidYield 94.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (60 mg) was added to a stirred solution of 4-hydroxycinnamic acid (325 mg, 1.98 mmol) in MeOH (15 mL) under an inert atmosphere. Hydrogen gas was then passed through the reaction mixture by means of a hydrogen filled bladder and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was filtered over celite and the celite was washed with MeOH. The filtrate was collected and concentrated under reduced pressure to afford 310 mg (94.5% yield) of 3-[4-hydroxy phenyl]propionic acid as a white solid. 1H NMR (DMSO): δ 7.0 (d, 2H), 6.6 (d, 2H), 2.35 (t, 2H), 2.25 (t, 2H), LC-MS purity: 96.55%.

Workup

  1. filtrationThe reaction mixture was filtered over celite
  2. washthe celite was washed with MeOH
  3. customThe filtrate was collected
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-db8daed5dce642949525372ec60ab98d
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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