Hydrochloric Acid → 4-(2-hydroxy-3,4-dimethoxyphenyl)isobenzofuran-1(3H)-one
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][O: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][O:14][C:15]2=[O:20]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a stirring solution of 4-(3,4-dimethoxy-2-(methoxymethoxy)phenyl)isobenzofuran-1(3H)-one (1.3 g, 3.9 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 and purification. The resulting residue purified by washings with pentane to afford the title compound as a solid.
Workup
- customthe resultant reaction mixture
- concentrationThe reaction mixture was concentrated under reduced pressure and basified with aq. sodium bicarbonate solution
- extractionextracted with ethyl acetate (3×)
- washThe combined ethyl acetate layer was washed with brine
- dry with materialdried over anhydrous sodium sulphate
- concentrationconcentrated under reduced pressure and purification
- customThe resulting residue purified by washings with pentane
Sources & evidence
- ORD record
- ord-0e8de8e253dc47108ab3199bda8d7e07
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09051290B2
Reaction notes
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