Sodium Hydroxide → 2-(Morpholin-4-yl)benzoic acid

HRID 1264604Notes

Reaction equation

HRID 1264604 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:17]=[CH:16][CH:15]=[CH:14][C:8]=2[C:9]([O:11]CC)=[O:10])[CH2:3][CH2:2]1.[OH-].[Na+]>O1CCCC1CCO>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[CH:17]=[CH:16][CH:15]=[CH:14][C:8]=2[C:9]([OH:11])=[O:10])[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 7148401ethyl 2-morpholinobenzoate

Product 1

HCID 27765612-(Morpholin-4-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 119895722-(Oxolan-2-yl)ethan-1-olSolvent

Procedure

Ethyl 2-morpholinobenzoate prepared in the manner described in Tetrahedron, 53:7557, (1997) was refluxed with 10 N NaOH in tetrahydrofuran-ethanol (8:2) for 1.5 hrs to give 2-morpholinobenzoic acid, mp 156-157° C. A 1.8 g sample of this compound in 5 ml of CH2Cl2 (chilled) was added a solution of 7.9 ml of oxalyl chloride in CH2Cl2 (2M) followed by the addition of 0.058 ml of N,N-dimethylformamide. The solution was stirred at room temperature for 6 hrs and the solvent removed. Toluene was added (2 times) and removed to give 2-(4-morpholino)benzoyl chloride as a yellow solid.

Sources & evidence

ORD record
ord-394fcda8c28c449bb22721c8e8160e7b
Source dataset
uspto-grants-2003_04
Patent number
US06544984B1

Reaction notes

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