Water → 2-Hydroxy-4-(4-morpholinyl)benzoic acid

HRID 884443Notes

Reaction equation

HRID 884443 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:6][C:5]=1[OH:16].O.O.[OH-].[Li+]>CO>[OH:16][C:5]1[CH:6]=[C:7]([N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[CH:8]=[CH:9][C:4]=1[C:3]([OH:17])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 9834610HCID 9834610, compound

Product 1

HCID 98559602-Hydroxy-4-(4-morpholinyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 2-hydroxy-4-morpholin-4-yl-benzoic acid methyl ester (4.6 g; 19.4 mmol) in MeOH (120 mL) was added water (60 mL) and lithium hydroxide hydrate (4.08 g; 97 mmol). The resulting mixture was heated to 80° C. for 15 hours. The resulting mixture then was washed with EtOAc (3×60 mL), and cooled to 0° C. and acidified with 2 N aqueous hydrochloric acid to pH 4. The resulting precipitate was collected on a Buchner funnel with suction, washed with water, and air dried to provide the acid (4.16 g; 96%).

Workup

  1. washThe resulting mixture then was washed with EtOAc (3×60 mL)
  2. temperaturecooled to 0° C.
  3. customThe resulting precipitate was collected on a Buchner funnel with suction
  4. washwashed with water, and air
  5. customdried
  6. customto provide the acid (4.16 g; 96%)

Sources & evidence

ORD record
ord-c96ded1140654f498d3436fed75aed8e
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Reaction notes

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