Hydrochloric Acid → 5-(4-Ethoxy-2-hydroxy-3-methoxyphenyl)isobenzofuran-1(3H)-one

HRID 2171132Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirring solution of 5-(4-ethoxy-3-methoxy-2-(methoxymethoxy)phenyl)isobenzofuran-1(3H)-one (100 mg, 0.292 mmol) in methanol (5 mL) was added conc. hydrochloric acid (0.5 mL) and heated to 50° C. for 1 h. The reaction mixture was concentrated under reduced pressure; the residue was basified with sodium bicarbonate solution and extracted with ethyl acetate (3×). The combined ethyl acetate layers were washed with brine, dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as a solid (60 mg, 68%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
extractionextracted with ethyl acetate (3×)
washThe combined ethyl acetate layers were washed with brine
dry with materialdried over sodium sulphate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-c5486f019ee74bf790f4bbc087addc82
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051290B2

Reaction notes

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