Lithium Hydroxide → 3-Methyl-4-(morpholin-4-yl)benzoic acid

HRID 336255Notes

Reaction equation

HRID 336255 reaction equation
[OH-].[Li+].[CH3:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[C:7]([O:9]C)=[O:8]>C1COCC1.O>[CH3:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67528858Methyl 3-methyl-4-morpholin-4-ylbenzoate

Product 1

HCID 184757233-Methyl-4-(morpholin-4-yl)benzoic acidYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Lithium hydroxide (2 g; 84.6 mmol; 5 eq.) was added to a solution of methyl 3-methyl-4-morpholin-4-ylbenzoate (4 g; 17 mmol; 1 eq.) in THF (100 mL) and water (5 mL) and the reaction mixture was stirred at 50° C. for 12 hours. The solvent was removed in vacuo, the residue diluted with water and the aqueous layer washed with DCM (2×50 mL). The aqueous layer was acidified to pH 4 with conc. HCl and extracted with ethyl acetate (2×100 mL). The combined organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo to afford the title compound (3.6 g, 97%) as a yellow solid.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue diluted with water
  3. washthe aqueous layer washed with DCM (2×50 mL)
  4. extractionextracted with ethyl acetate (2×100 mL)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3301824e00444f38bde6af581aebf56c
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

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