Hydrochloric Acid → 2-(2-Methoxyphenyl)-3-phenylpropanoic acid

HRID 335020Notes

Reaction equation

HRID 335020 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10]([O:12]C)=[O:11].[OH-].[Na+].O.Cl>C1COCC1.CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10]([OH:12])=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 66695010Methyl 2-(2-methoxyphenyl)-3-phenylpropanoate

Product 1

HCID 242561472-(2-Methoxyphenyl)-3-phenylpropanoic acidYield 51.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(2-methoxyphenyl)-3-phenylpropanoate (4.433 g, 16 mmol, 1 eq) is dissolved in 100 mL of a 1:1 (v:v) mixture of THF and methanol. Sodium hydroxide (3.28 g, 82 mmol, 5 eq) is added and the reaction mixture is stirred 18 hours at room temperature. The reaction is then poured into H2O and the pH is adjusted to 2 via addition of 1N HCl. A white precipitate forms which is removed by filtration. The resulting solution is extracted with 3 portion of diethyl ether. The extracts are pooled, washed with H2O and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue is purified over silica to afford 2.107 g (51%) of the desired compound. ESI− MS 255 (M−1), 211 (M-CO2H).

Workup

  1. customA white precipitate forms which is removed by filtration
  2. extractionThe resulting solution is extracted with 3 portion of diethyl ether
  3. washwashed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue is purified over silica

Sources & evidence

ORD record
ord-7e0f8bcefbce42dfb670c340f5ab24c5
Source dataset
uspto-grants-2014_11
Patent number
US08883832B2

Reaction notes

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