Hydrochloric Acid → 3-(2-Hydroxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane

HRID 650419Notes

Reaction equation

HRID 650419 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:18]4[C:13](=[CH:14][C:15]([O:19][CH2:20][CH2:21][CH3:22])=[CH:16][CH:17]=4)[CH2:12][CH2:11]3)=[CH:4][C:3]=2[O:2]1.Cl.[CH3:24][OH:25]>>[OH:25][C:24]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[CH:12]1[C:13]2[C:18](=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH2:21][CH3:22])[CH:14]=2)[CH:10]([C:5]2[CH:6]=[CH:7][C:8]3[O:9][CH2:1][O:2][C:3]=3[CH:4]=2)[CH2:11]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 184276791-(3,4-Methylenedioxyphenyl)-5-(prop 1-yloxy)indane

Product 1

HCID 217130923-(2-Hydroxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indaneYield 94%

Procedure

To a solution of (1RS,3RS)-3-((2-methoxymethoxy)-4-methoxyphenyl)]-1-(3,4-methylenedioxyphenyl)-5-(prop 1-yloxy)indane (0.075 g, 0.16 mmol) in methanol (5 ml) was added 4-5 drops of 6M-HCl and the mixture refluxed for 1.5 h under argon. The solvent was removed in vacuo and the product partitioned between EtOAc and water. The organic extract was washed with water then sat. aq. NaHCO3 solution and finally brine. After drying (MgSO4 anhydrous) filtration and evaporation gave the title compound (0.064 g, 94%).

Workup

  1. temperaturethe mixture refluxed for 1.5 h under argon
  2. customThe solvent was removed in vacuo
  3. customthe product partitioned between EtOAc and water
  4. extractionThe organic extract
  5. washwas washed with water
  6. customAfter drying
  7. filtration(MgSO4 anhydrous) filtration and evaporation

Sources & evidence

ORD record
ord-81515baafe2c4da485eaee2e104ba482
Source dataset
uspto-grants-2001_08
Patent number
US06271399B1

Reaction notes

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