Sodium Hydroxide → 3-(3-methoxy-4-methylphenyl)propanoic acid

HRID 1859806Notes

Reaction equation

HRID 1859806 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][C:18]=1[CH3:19])[CH2:6][CH:7](C(OC)=O)[C:8]([O:10]C)=[O:9].[OH-].[Na+]>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[CH:16]=[CH:17][C:18]=1[CH3:19]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18626507HCID 18626507, compound

Product 1

HCID 31636013-(3-methoxy-4-methylphenyl)propanoic acidYield 123%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 25.84 g (0.1072 mol) of dimethyl 2-(3-methoxy-4-methylbenzyl)malonate in 150 mL of MeOH was treated with a solution of 20 g (0.5 mol) of NaOH in 100 mL of H2O and heated at reflux overnight. The solution was concentrated under reduced pressure and the residue taken up in H2O and washed with Et2O. The solution was acidified to Congo Red end point with dilute HCl and the solution extracted with Et2O. The Et2O was washed with saturated NaCl and dried over MgSO4. Removal of the solvent under reduced pressure gave 25.6 g of an oil. This was taken up in 125 mL of dioxane and heated at reflux overnight. Removal of the solvent under reduced pressure gave 20.5 g of the crude product. Chromatography on silica gel, eluting with CHCl3/MeOH (98/2) gave 8.65 g (41.6% yield) of the product as a white solid, mp 80-82° C. The structure was confirmed by NMR and mass spectroscopy. MS m/z 195 (M+H+).

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. concentrationThe solution was concentrated under reduced pressure
  4. washwashed with Et2O
  5. extractionthe solution extracted with Et2O
  6. washThe Et2O was washed with saturated NaCl
  7. dry with materialdried over MgSO4
  8. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-f31edde82dad4ca1bc8eca6d1248d2d3
Source dataset
uspto-grants-2003_03
Patent number
US06528535B2

Reaction notes

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