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

HRID 1714515Notes

Reaction equation

HRID 1714515 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-aa566a0a7ba9421d9c6fdeab7e1df1a2
Source dataset
uspto-grants-2010_09
Patent number
US07795444B2

Reaction notes

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