(Z)-3-(4-(2-methoxyethyl)phenoxy)acrylic acid → 3-[4-(2-Methoxyethyl)phenoxy]propanoic acid

HRID 919022Notes

Reaction equation

HRID 919022 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:16]=[CH:15][C:8]([O:9]/[CH:10]=[CH:11]\[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1>CCO.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:16]=[CH:15][C:8]([O:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 86646353(Z)-3-(4-(2-methoxyethyl)phenoxy)acrylic acid

Product 1

HCID 167712623-[4-(2-Methoxyethyl)phenoxy]propanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(E)/(Z)-3-(4-(2-methoxyethyl)phenoxy)acrylic acid (0.3 g) was dissolved in EtOH (10 mL) and Pd/C (5%, degussa type E101, 40 mg) was added. The mixture was hydrogenated at atmospheric pressure for 2 hours and then filtered and the solvent removed to dryness. After purification by column chromatography using a mixture of hexane/ethyl acetate, 3-(4-(2-methoxyethyl)phenoxy)propanoic acid was obtained as a white solid (0.236 g). 1H NMR (CDCl3, 400 mHz, ppm); 2.85 (t, 4H), 3.35 (s, 3H), 3.55 (t, 2H), 4.25 (t, 2H), 6.85 (d, 2H), 7.1 (d, 2H).

Workup

  1. filtrationfiltered
  2. customthe solvent removed to dryness
  3. customAfter purification by column chromatography
  4. additiona mixture of hexane/ethyl acetate

Sources & evidence

ORD record
ord-5e8d11dcdba04408bcc73dc8f207f02c
Source dataset
uspto-grants-2016_03
Patent number
US09272996B2

Reaction notes

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