Methanol → (6-Methoxy-3-oxo-indan-1-yl)-acetic acid methyl ester

HRID 1519185Notes

Reaction equation

HRID 1519185 reaction equation
S(=O)(=O)(O)O.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]2[C:14]([CH2:16][CH:17]([CH2:18][C:19]([OH:21])=[O:20])[C:10]=2[CH:9]=1)=[O:15].[CH3:22]O>>[CH3:22][O:20][C:19](=[O:21])[CH2:18][CH:17]1[C:10]2[C:11](=[CH:12][CH:13]=[C:8]([O:7][CH3:6])[CH:9]=2)[C:14](=[O:15])[CH2:16]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2125262,3-Dihydro-6-methoxy-3-oxo-1H-indene-1-acetic acid

Product 1

HCID 15751354(6-Methoxy-3-oxo-indan-1-yl)-acetic acid methyl ester

Procedure

Concentrated sulfuric acid (3.0 mL) is added to 5-methoxy-1-indanone-3-acetic acid (13.0 g) dissolved in methanol (100 mL). The solution is stirred at reflux temperature for 4 h and then cooled to room temperature. About two third of the methanol is removed under reduced pressure and water (100 mL) and ethyl acetate (200 mL) are added to the remainder. The organic phase is separated and washed with water, 1 M NaOH solution, and brine. The organic phase is dried (MgSO4) and the solvent is evaporated to give the product as a yellow oil.

Workup

  1. temperatureat reflux temperature for 4 h
  2. customAbout two third of the methanol is removed under reduced pressure and water (100 mL) and ethyl acetate (200 mL)
  3. additionare added to the remainder
  4. customThe organic phase is separated
  5. washwashed with water, 1 M NaOH solution, and brine
  6. dry with materialThe organic phase is dried (MgSO4)
  7. customthe solvent is evaporated

Sources & evidence

ORD record
ord-468cad9d1a6a49dabcad511314db2f65
Source dataset
uspto-grants-2015_07
Patent number
US09073870B2

Reaction notes

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