Lithium hydroxide, monohydrate → 2-(3-(Morpholin-4-yl)phenyl)acetic acid

HRID 1017566

Reaction equation

HRID 1017566 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]([CH2:13][C:14]([O:16]C)=[O:15])[CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.O.[OH-].[Li+]>CO.O>[N:1]1([C:7]2[CH:8]=[C:9]([CH2:13][C:14]([OH:16])=[O:15])[CH:10]=[CH:11][CH:12]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 18403524Methyl 3-(morpholin-4-yl)phenylacetate

Product 1

HCID 184034952-(3-(Morpholin-4-yl)phenyl)acetic acidYield 90.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-(morpholin-4-yl)phenylacetate (0.50 g, 2.1 mmol) in methanol (5 mL) and H2O (1 mL) was added lithium hydroxide monohydrate (0.18 g, 2 eq.). After the reaction mixture was stirred at room temperature overnight, it was concentrated to dryness. Acetic acid was then added to the residue and the resulting mixture was partitioned between EtOAc and H2O. The organic layer was washed with NaCl (sat.), dried over Na2SO4, and evaporation under vacuo to give 3-(morpholin-4-yl)phenylacetic acid (0.42 g).

Workup

  1. concentrationit was concentrated to dryness
  2. additionAcetic acid was then added to the residue
  3. customthe resulting mixture was partitioned between EtOAc and H2O
  4. washThe organic layer was washed with NaCl (sat.)
  5. dry with materialdried over Na2SO4, and evaporation under vacuo

Sources & evidence

ORD record
ord-7f308cfca37b4e56b5b18d8b5d2b2669
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Linked notes

Loading…