Veratrole → 5,6-Dimethoxy-3-methyl-2,3-dihydro-1H-inden-1-one

HRID 1793776Notes

Reaction equation

HRID 1793776 reaction equation
[C:1]1([O:9][CH3:10])[C:2](=[CH:5][CH:6]=[CH:7][CH:8]=1)[O:3][CH3:4].[CH:11]([CH2:13][C:14](O)=[O:15])=[CH2:12]>>[CH3:4][O:3][C:2]1[CH:5]=[C:6]2[C:7](=[CH:8][C:1]=1[O:9][CH3:10])[C:14](=[O:15])[CH2:13][CH:11]2[CH3:12]

Participants

3

Reactant 2

HCID 7043VeratroleHCID 327433-Butenoic acid

Product 1

HCID 6057815,6-Dimethoxy-3-methyl-2,3-dihydro-1H-inden-1-oneYield 74%

Conditions

Temperature
60 °C

Procedure

A mixture of 19.1 ml (150 mmol) of veratrol and 19.2 ml (225 mmol) of vinylacetic acid in 230 g of 83% polyphosphoric acid was stirred for 15 h at 60° C. and then poured into 500 ml of ice water. After 30 minutes (min) of stirring, the product was extracted three times, each time with 200 ml of ether. The combined organic phases were washed twice, each time with 100 ml of 2N NaOH, once with 100 ml of water and once with 50 ml of saturated sodium chloride solution, dried over sodium sulfate and freed from solvent on a rotary evaporator. After recrystallizing the residue (in AcOEt/pentane), 22.8 g (74%) of 5,6-dimethoxy-3-methylindan-1-one were obtained.

Workup

  1. stirringAfter 30 minutes (min) of stirring
  2. extractionthe product was extracted three times
  3. washThe combined organic phases were washed twice
  4. dry with materialeach time with 100 ml of 2N NaOH, once with 100 ml of water and once with 50 ml of saturated sodium chloride solution, dried over sodium sulfate
  5. customfreed from solvent on a rotary evaporator
  6. customAfter recrystallizing the residue (in AcOEt/pentane)

Sources & evidence

ORD record
ord-2d88900d50a349038d828ee8f06af057
Source dataset
uspto-grants-2006_04
Patent number
US07022664B2

Reaction notes

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