Ethanol → 1,3-Benzodioxole-5-acetic acid, ethyl ester

HRID 1533266Notes

Reaction equation

HRID 1533266 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11]([OH:13])=[O:12])=[CH:4][C:3]=2[O:2]1.S(=O)(=O)(O)O.[CH2:19](O)[CH3:20]>>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11]([O:13][CH2:19][CH3:20])=[O:12])=[CH:4][C:3]=2[O:2]1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 76115Benzo-1,3-dioxole-5-acetic acid

Product 1

HCID 5845741,3-Benzodioxole-5-acetic acid, ethyl ester

Procedure

To a solution of 3,4-methylenedioxyphenylacetic acid (10 g) in ethanol (100 ml) was added conc. sulfuric acid (3 ml). After being refluxed for 90 minutes, the mixture was concentrated in vacuo. The residue was dissolved in diethyl ether (150 ml). The solution was washed with 1M aqueous sodium bicarbonate solution and brine successively and dried over magnesium sulfate, and concentrated in vacuo to give ethyl 3,4-methylenedioxyphenylacetate (11.0 g) as an oil.

Workup

  1. temperatureAfter being refluxed for 90 minutes
  2. concentrationthe mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in diethyl ether (150 ml)
  4. washThe solution was washed with 1M aqueous sodium bicarbonate solution and brine successively
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9de0592d6a694eccb697922f120a0767
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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