Hydrochloric Acid → 4-(2-Hydroxy-3,4-dimethoxy-phenyl)-indan-1-one

HRID 2171011Notes

Reaction equation

HRID 2171011 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:21]COC)=[C:5]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][CH2:14][C:15]3=[O:20])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl>CO>[OH:21][C:4]1[C:3]([O:2][CH3:1])=[C:8]([O:9][CH3:10])[CH:7]=[CH:6][C:5]=1[C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH2:13][CH2:14][C:15]2=[O:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866775744-(3,4-Dimethoxy-2-methoxymethoxy-phenyl)-indan-1-one

Product 1

HCID 674668064-(2-Hydroxy-3,4-dimethoxy-phenyl)-indan-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a stirring solution of 4-(3,4-Dimethoxy-2-methoxymethoxy-phenyl)-indan-1-one (1.6 g, 4.87 mmol) in methanol (15 mL) at 0° C., was added concentrated hydrochloride acid (3 mL) and the resultant reaction mixture was stirred at 50° C. for 15 min. The reaction mixture was concentrated under reduced pressure and basified with aq sodium bicarbonate solution extracted with ethyl acetate (3×). The combined ethyl acetate layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue was purified by washing with ether to afford the title compound as a solid.

Workup

  1. customthe resultant reaction mixture
  2. concentrationThe reaction mixture was concentrated under reduced pressure and basified with aq sodium bicarbonate solution
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined ethyl acetate layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified
  8. washby washing with ether

Sources & evidence

ORD record
ord-5e129c83fb604004b284a3d3f3b832fe
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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