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

HRID 585667Notes

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 equipped with magnetic stirrer was loaded with (±)-{4-[2,4-bis(methoxymethoxy)phenyl]cyclohexylidene}acetic acid (25 mg, 74 mmol), 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 a yellow oil (15 mg) which was purified by preparative TLC (ethyl acetate/petroleum ether, 3:1, v/v), furnishing the title compound (6.5 mg, 35%) as an oil. m/z (ES+) 339 (M+H+).

Workup

customA round bottomed flask equipped with magnetic stirrer
filtrationThe reaction mixture was filtered through a celite plug
washwashing with methanol
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-8a935e4d779d410699abe063bc8925ec
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06933319B2

Reaction notes

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