Sulfuric Acid → Methyl 2-(1,3-dioxaindan-5-yl)acetate

HRID 442656Notes

Reaction equation

HRID 442656 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.[C:19]([O-])(O)=O.[Na+]>CO>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11]([O:13][CH3:19])=[O:12])=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 76115Benzo-1,3-dioxole-5-acetic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 266588Methyl 2-(1,3-dioxaindan-5-yl)acetateYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,4-methylenedioxyphenylacetic acid (4.2 g, 23 mmol) in methanol (50 mL) was added concentrated sulfuric acid (1.5 mL). The mixture was refluxed for 48 h, cooled to room temperature, and neutralized with saturated NaHCO3. The methanol was removed in vacuo. The residue was extracted with 1:1 hexane/EtOAc (2×100 mL). The combined organic phase was washed with water, saturated NaHCO3, and brine, and dried over Na2SO4. The solvent was removed in vacuo to yield the title compound as an oil (3.9 g, 86%). 1H NMR (CDCl3) 6.78-6.72 (m, 3H), 5.95 (s, 2H), 3.69 (s, 3H), 3.54 (s, 2H).

Workup

  1. temperatureThe mixture was refluxed for 48 h
  2. customThe methanol was removed in vacuo
  3. extractionThe residue was extracted with 1:1 hexane/EtOAc (2×100 mL)
  4. washThe combined organic phase was washed with water, saturated NaHCO3, and brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-9ce470a48d4241289b3ac28f53610f43
Source dataset
uspto-grants-1999_04
Patent number
US05891871

Reaction notes

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