Veratrole → 3-Ethyl-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

HRID 1714449

Reaction equation

HRID 1714449 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10].[C:11](O)(=[O:16])[CH2:12][CH:13]=[CH:14][CH3:15]>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][C:4]=1[O:9][CH3:10])[C:11](=[O:16])[CH2:12][CH:13]2[CH2:14][CH3:15]

Participants

3

Reactant 2

HCID 7043Veratrole2×HCID 212633-Pentenoic acid2×

Product 1

HCID 184456823-Ethyl-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

Conditions

Temperature
60 °C

Procedure

A mixture of 1,2-dimethoxy-benzene (Compound 47a) (21.9 mL, 0.170 mole) and pent-3-enoic acid (Compound 47b) (25.5 g, 0.255 mole) was stirred under argon in an ice bath. Polyphosphoric acid (230 g, 1.05 mole) was added slowly. After addition was complete, the ice bath was removed and the reaction heated for 16 hours at 60° C. The reaction was added to ice water and extracted with dichloromethane. The organic extracts were washed with 3N NaOH, water, brine and dried over Na2SO4. The solvent was then removed in vacuo to yield a red oil containing the crude title compound. The crude material was purified on a silica gel column using dichloromethane as eluent. The pure fractions were combined and concentrated to yield the racemic mixture of the title compound as an off-white solid. MS m/z 221 (M+H)+;

Workup

  1. additionAfter addition
  2. customthe ice bath was removed
  3. additionThe reaction was added to ice water
  4. extractionextracted with dichloromethane
  5. washThe organic extracts were washed with 3N NaOH, water, brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent was then removed in vacuo
  8. customto yield a red oil

Sources & evidence

ORD record
ord-baf7d84ba9d0448597691c500386f2fc
Source dataset
uspto-grants-2010_09
Patent number
US07795440B2

Linked notes

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