Methanol → HCID 89581234, compound

HRID 1501165Notes

Reaction equation

HRID 1501165 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].O1CCCC1.CO.O.[OH-].[Li+]>O>[CH3:1][C:2]1[CH:11]=[C:10]([CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 89580877HCID 89580877, compound

Product 1

HCID 89581234HCID 89581234, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl 2-methyl-4-(piperidin-1-ylmethyl)benzoate (1.8 g, 7.3 mmol) in the mixture solution of tetrahydrofuran:methanol:water=3:1:1 (20 mL) was added lithium hydroxide monohydrate (1 g, 42 mmol). The mixture was stirred at room temperature for 2 hours. The suspension was concentrated in vacuo and quenched with hydrochloride acid aqueous (1N, 5 mL). To the residue, water (50 mL) was added. The mixture was extracted with dichloromethane (50 mL). The combined organic phase was separated, dried over sodium sulfate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, methanol/dichloromethane=1:15) to give the product 2-methyl-4-(piperidin-1-ylmethyl)benzoic acid (360 mg, 21%) as pale solid.

Workup

  1. concentrationThe suspension was concentrated in vacuo
  2. customquenched with hydrochloride acid aqueous (1N, 5 mL)
  3. additionTo the residue, water (50 mL) was added
  4. extractionThe mixture was extracted with dichloromethane (50 mL)
  5. customThe combined organic phase was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a residue
  10. customThe residue was purified by column chromatography (silica gel, methanol/dichloromethane=1:15)

Sources & evidence

ORD record
ord-caf1c07ce2244f70af5af05d60ae517e
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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