Water → 2-Methoxy-5-(morpholin-4-yl)benzoic acid

HRID 1012163Notes

Reaction equation

HRID 1012163 reaction equation
C[O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[O:16][CH3:17].O.[OH-].[Na+]>CO>[CH3:17][O:16][C:5]1[CH:6]=[CH:7][C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:9][C:4]=1[C:3]([OH:18])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67105971Methyl 2-methoxy-5-(morpholin-4-yl)benzoate

Product 1

HCID 298884132-Methoxy-5-(morpholin-4-yl)benzoic acidYield 56.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-methoxy-5-morpholin-4-yl-benzoic acid methyl ester (170 mg) was dissolved in MeOH (5 ml) and H2O (5 ml) and treated with 1 M aq. sodium hydroxide (2 ml). After stirring at r.t. for 16 h the mixture was concentrated and partitioned between EtOAc and H2O. the aqueous layer was acidified (pH 2.0) and then extracted further with EtOAc (×3). The combined organic fraction was washed with brine, dried (MgSO4) and reduced in vacuo to give 2-methoxy-5-morpholin-4-yl-benzoic acid (90 mg) as a yellow oil. (LC/MS (basic method): Rt 0.91 min., [M+H]+ 238).

Workup

  1. concentrationwas concentrated
  2. custompartitioned between EtOAc and H2O
  3. extractionextracted further with EtOAc (×3)
  4. washThe combined organic fraction was washed with brine
  5. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-47b3096d97c14daf90158ecea1b8fc15
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

Loading…