p-Toluenesulfonic acid → Ethyl 3-methoxy-4-methylphenylacetate

HRID 516861

Reaction equation

HRID 516861 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11]([OH:13])=[O:12])[CH:6]=[CH:7][C:8]=1[CH3:9].[CH3:14][C:15]1C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 91183902-(3-Methoxy-4-methylphenyl)acetic acid

Product 1

HCID 21079756Ethyl 3-methoxy-4-methylphenylacetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 2-(3-methoxy-4-methylphenyl)acetic acid (Step A, 4.64 g, 25.7 mmol) in ethanol (100 ml) was added p-TsOH (0.7 g, 3.7 mmol) at room temperature under argon and the reaction mixture was refluxed for 12 hours or until all the starting material is consumed, concentrated, diluted in EtOAc and washed with 0.1N HCl, brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (hexane:ethyl acetate, 2:1) to give the title compound.

Workup

  1. temperaturethe reaction mixture was refluxed for 12 hours or until all the starting material
  2. customis consumed
  3. concentrationconcentrated
  4. additiondiluted in EtOAc
  5. washwashed with 0.1N HCl, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by flash chromatography on a silica gel column (hexane:ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-825aa86bdae84b0cac58a6d2d8eb79cb
Source dataset
uspto-grants-2015_08
Patent number
US09115072B2

Linked notes

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