(+/-)-{4-[2,4-Bis(methoxymethoxy)phenyl]cyclohexylidene}acetic acid → {4-[2,4-Dihydroxyphenyl]cyclohexylidene}acetic acid

HRID 1263525Notes

Reaction equation

COC[O:4][C:5]1[CH:10]=[C:9]([O:11]COC)[CH:8]=[CH:7][C:6]=1[CH:15]1[CH2:20][CH2:19][C:18](=[CH:21][C:22]([OH:24])=[O:23])[CH2:17][CH2:16]1>CO>[OH:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[CH:15]1[CH2:16][CH2:17][C:18](=[CH:21][C:22]([OH:24])=[O:23])[CH2:19][CH2:20]1

Participants

Conditions

Temperature: 60 °C

Procedure

A round bottomed flask was charged with (±)-{4-[2,4-bis(methoxymethoxy)phenyl]cyclohexylidene}acetic acid (25 mg), acidic Dowex resin (75 mg) and methanol (15 ml) then stirred at 60° C. for 3 hr. The reaction mixture was filtered through a celite plug, washing with methanol. The solvent was removed under reduced pressure to give an oil which was purified by preparative TLC (ethyl acetate/petroleum ether, 3:1, v/v), furnishing the title compound (6.5mg, 35%) as an oil. δH (CD3OD) 1.22-1.40 (2H, m), 1.90-2.10 (4H, m), 2.36-2.40 (2H, m), 3.08 (1H, tt), 5.62 (1H, s), 6.20 (1H, dd), 6.25 (1H, d), 6.84 (1H, d); m/z(ES+) 339 (M+H+).

Workup

filtrationThe reaction mixture was filtered through a celite plug
washwashing with methanol
customThe solvent was removed under reduced pressure
customto give an oil which
customwas purified by preparative TLC (ethyl acetate/petroleum ether, 3:1

Sources & evidence

ORD record: ord-9b593da3c93842628944ba91757ffc8a
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06541473B2

Reaction notes

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