3-(2,3-Dimethoxyphenyl)propanoic acid → 4,5-Dimethoxy-1-indanone

HRID 2185636

Reaction equation

HRID 2185636 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][CH2:12][C:13]([OH:15])=O>CS(O)(=O)=O>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[C:5]2[C:4]=1[CH2:11][CH2:12][C:13]2=[O:15]

Participants

3

Reactant 1

HCID 3149293-(2,3-Dimethoxyphenyl)propanoic acid

Product 1

HCID 2404464,5-Dimethoxy-1-indanoneYield 65.6%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

Under nitrogen a solution of 3-(2,3-dimethoxyphenyl)-propanoic acid (2 g) in 50 ml methanesulfonic acid was warmed at 60° C. and kept there for 2 hours. The reaction mixture was cooled to room temperature and poured into ice/water. After extraction with ethyl acetate the organic layer was washed with a 1N aqueous sodium hydroxyde solution, dried over magnesium sulfate, filtered and evaporated in vacuo yielding 1.2 g of 2,3-dihydro4,5-dimethoxy-1H-inden-1-one, M.S. (C.I.) (M/Z): 193 [M+H]+.

Workup

  1. extractionAfter extraction with ethyl acetate the organic layer
  2. washwas washed with a 1N aqueous sodium hydroxyde solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-8f0b5d6efdc74a3da2921db41a761b9e
Source dataset
uspto-grants-2002_06
Patent number
US06403573B1

Linked notes

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