Methanol → Benzeneacetic acid, 3,4-dimethoxy-, methyl ester

HRID 1620141Notes

Reaction equation

HRID 1620141 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([OH:14])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:15]O>S(=O)(=O)(O)O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 887MethanolHCID 7139(3,4-Dimethoxyphenyl)acetic acid

Product 1

HCID 85213Benzeneacetic acid, 3,4-dimethoxy-, methyl esterYield 96%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a solution of 2-(3,4-dimethoxyphenyl)acetic acid (25.0 g, 127.4 mmol) in MeOH (100 mL) in a 500 mL round-bottomed flask equipped with a magnetic stirrer was added a catalytic amount of sulfuric acid (around 10 drops) and the mixture was stirred overnight under reflux. After cooling to RT, MeOH was removed at 40° C. under vacuum and the product was taken up in CH2Cl2 (250 mL), washed with water (5×20 mL), brine (20 mL), dried over Na2SO4, filtered, and concentrated under vacuum to give methyl 2-(3,4-dimethoxyphenyl)acetate SLA 28134 as an orange oil (25.77 g, 96% yield).

Workup

  1. temperatureunder reflux
  2. customMeOH was removed at 40° C. under vacuum
  3. washwashed with water (5×20 mL), brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5fd0f1b0134341e7991f0b21c1dc3260
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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