Methanol → Methyl 3-(4-methoxyphenyl)propanoate

HRID 1089368Notes

Reaction equation

HRID 1089368 reaction equation
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:9][CH:8]=1.[CH3:18]O>>[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 957503-(p-Methoxyphenyl)propionic acid

Product 1

HCID 300018Methyl 3-(4-methoxyphenyl)propanoate

Procedure

Thionyl chloride (3.1 ml, 42.5 mmol) was added slowly to methanol (30 ml) with stirring under cooling with a Dry Ice/methanol bath. After allowing the reaction to warm to room temperature, 3-(4-methoxyphenyl)propionic acid (5 g, 27.7 mmol) was added and stirred for an additional 1 hour. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate. The solution was washed twice with a saturated aqueous solution of sodium bicarbonate, then once with a saturated aqueous solution of sodium chloride. After drying over unhydrous sodium sulfate, the solvent was evaporated in vacuo to produce a pale yellow crystal in an amount of 5.29 g (yield, 98%). Rf1 : 0.83

Workup

  1. temperatureunder cooling with a Dry Ice/methanol bath
  2. customthe reaction
  3. stirringstirred for an additional 1 hour
  4. customThe solvent was removed in vacuo
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washThe solution was washed twice with a saturated aqueous solution of sodium bicarbonate
  7. dry with materialAfter drying over unhydrous sodium sulfate
  8. customthe solvent was evaporated in vacuo
  9. customto produce a pale yellow crystal
  10. customin an amount of 5.29 g (yield, 98%)

Sources & evidence

ORD record
ord-4fff79cbbbc643ce85078d63c0701996
Source dataset
uspto-grants-1990_10
Patent number
US04965405

Reaction notes

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