1-[3-Benzo[1,3]dioxol-5-yl-5-(4-methoxy-benzyloxy)-phenyl]-propan-1-one → 1-(3-Benzo[1,3]dioxol-5-yl-5-hydroxy-phenyl)-propan-1-one

HRID 417051Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:11]=[C:12]([C:26](=[O:29])[CH2:27][CH3:28])[CH:13]=[C:14]([O:16]CC4C=CC(OC)=CC=4)[CH:15]=3)=[CH:9][C:4]=2[O:3][CH2:2]1>C(O)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:11]=[C:12]([C:26](=[O:29])[CH2:27][CH3:28])[CH:13]=[C:14]([OH:16])[CH:15]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

Conditions

Temperature: 100 °C

Procedure

1-[3-Benzo[1,3]dioxol-5-yl-5-(4-methoxy-benzyloxy)-phenyl]-propan-1-one (135 mg) was dissolved in glacial acetic acid (2 mL) and heated at 100° C. for 2 days. The solvent was removed under reduced pressure and the residue was purified on a silica gel column using ethyl acetate and hexanes to yield 28.5 mg of the title compound (30% yield). HRMS calcd for C16H14O4 [M+H]+ 271.0965, observed 271.0964.

Workup

customThe solvent was removed under reduced pressure
customthe residue was purified on a silica gel column

Sources & evidence

ORD record: ord-953022c327134b66b122637cb69f4e8b
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088936B2

Reaction notes

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