Water → 4-(cis-2-Phenyl-1-cyclohexanoyloxy)-2-methoxy-benzoic acid

HRID 1678

Reaction equation

[C:1]1([C@H:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]2[C:13]([O:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[C:18]([O:26][CH3:27])[CH:17]=2)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.O[Li].O>C1COCC1>[C:1]1([C@H:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]2[C:13]([O:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([OH:22])=[O:21])=[C:18]([O:26][CH3:27])[CH:17]=2)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a stirred solution of methyl 4-(cis-2-phenyl- 1-cyclohexanoyloxy)-2-methoxybenzoate (230 mg, 0.64 mmol) in THF:H2O (5 mL:1 mL) was added LiOH.H2O (113.5 mg, 2.7 mmol). The reaction was heated to 45° C. over 12 h and then cooled to ambient temperature. The solvent was removed under reduced pressure. The crude solid was passed through a small plug of silca gel packed in 90:10 CH2Cl2 :MeOH(NH3) and eluted with same. The solvent was removed under reduced pressure to afford 4-(cis-2-phenyl-1-cyclohexanoyloxy)-2-methoxy-benzoic acid as a foam.

Workup

temperaturecooled to ambient temperature
customThe solvent was removed under reduced pressure
washMeOH(NH3) and eluted with same
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-9cf6d25d3c4e47a1a40710053bd23b71
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05726172

Linked notes

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