Water → 4-(4-Tetrahydropyranoyloxy)-2-methoxy-benzoic acid

HRID 1675

Reaction equation

HRID 1675 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[C:12]([O:20][CH3:21])[CH:11]=2)=[O:8])[CH2:3][CH2:2]1.O.O[Li].O>C1COCC1>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([OH:16])=[O:15])=[C:12]([O:20][CH3:21])[CH:11]=2)=[O:8])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 57075614Methyl 4-(4-tetrahydropyranoyloxy)-2-methoxy-benzoate

Product 1

HCID 571011474-(4-Tetrahydropyranoyloxy)-2-methoxy-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a stirred solution of methyl 4-(4-tetrahydropyranoyloxy)-2-methoxy-benzoate (369 mg, 1.38 mmol) in THF:H2O (2.5 mL: 0.5 mL) was added LiOH.H2O (116.4 mg, 2.77 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 80:20 hexanes:EtOAc and eluted with 50:50 hexanes:EtOAc. The solvent was removed under reduced pressure to afford 4-(4-tetrahydropyranoyloxy)-2-methoxy-benzoic acid as a foam.

Workup

  1. temperaturecooled to ambient temperature
  2. customThe solvent was removed under reduced pressure
  3. washEtOAc and eluted with 50:50 hexanes
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-effcf6e5366a4bfca9b4bac40907f32c
Source dataset
uspto-grants-1998_03
Patent number
US05726172

Linked notes

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