3-(3,4-Dimethoxyphenyl)propionic acid → 5,6-Dimethoxy-1-indanone

HRID 1698464Notes

Reaction equation

HRID 1698464 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]([OH:15])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][C:8]=1[O:9][CH3:10])[C:13](=[O:15])[CH2:12][CH2:11]2

Participants

3

Reactant 1

HCID 750193-(3,4-Dimethoxyphenyl)propionic acid

Product 1

HCID 750185,6-Dimethoxy-1-indanoneYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

For example, Non-Patent Document 1 discloses that 1 g of 3-(3,4-dimethoxyphenyl)propionic acid and 10 g of polyphosphoric acid were reacted at 65° C. for 25 minutes, followed by addition of cold water. Then, the resulting mixture was extracted with diethyl ether or ethyl acetate, and the organic layer thus extracted was washed with a 10% aqueous solution of sodium bicarbonate and purified by crystallization with ethanol to give 0.812 g (yield 90%) of 5,6-dimethoxy-1-indanone. However, it is also reported that the yield dropped to 71% when the reaction time was extended to 70 minutes in the above method. Generally, each unit operation is time-consuming in an industrial-scale production, and thus, it is difficult to perform operations in such a way that reactions are completed within only several tens of minutes. In view of the foregoing, the method described in the above document is far from an industrially efficient production method.

Workup

  1. customwere reacted at 65° C. for 25 minutes
  2. extractionThen, the resulting mixture was extracted with diethyl ether or ethyl acetate
  3. extractionthe organic layer thus extracted
  4. washwas washed with a 10% aqueous solution of sodium bicarbonate
  5. custompurified by crystallization with ethanol

Sources & evidence

ORD record
ord-0f1e2377481d43c198ec813d29719af9
Source dataset
uspto-grants-2012_04
Patent number
US08163962B2

Reaction notes

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