Water → 2-(4-Methoxyphenyl)prop-2-enoic acid

HRID 1859308Notes

Reaction equation

HRID 1859308 reaction equation
O[C:2]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)([CH3:6])[C:3]([OH:5])=[O:4].S(=O)(=O)(O)O.O>O1CCOCC1>[CH3:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([C:2](=[CH2:6])[C:3]([OH:5])=[O:4])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 131581022-Hydroxy-2-(4-methoxyphenyl)propanoic acid

Product 1

HCID 145737872-(4-Methoxyphenyl)prop-2-enoic acidYield 78.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Hydroxy-2-(4-methoxyphenyl)propionic acid (35 g, 178 mmol) was dissolved in dioxane (700 ml) and concentrated sulfuric acid (60 ml) was added thereto. The reaction mixture was refluxed for 2 hours under heating. The reaction solution was cooled and, after adding water, extracted with ethyl acetate. The organic layer was washed with saturated sodium thiosulfate solution and water, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 24.8 g (yield: 72%) of the title compound as a brown solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. temperatureunder heating
  3. temperatureThe reaction solution was cooled
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated sodium thiosulfate solution and water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-682fd67c9479434aa8ebc41887bd4154
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

Loading…