Lithium Hydroxide → HCID 8122187, compound

HRID 1643311Notes

Reaction equation

HRID 1643311 reaction equation
[CH2:1]([N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:19]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]1[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 2723671Tetrabutylammonium HydroxideHCID 57857121HCID 57857121, compound

Product 1

HCID 8122187HCID 8122187, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(dibenzylamino)benzoate (52 mg, 0.16 mmol) in a 2:1 mixture of THF/dH2O was added LiOH (10 mg, 0.48 mmol). Tetra-butyl ammonium hydroxide (2 mL, 0.1N solution in toluene/MeOH) was added to the reaction and allowed to stir at room temperature for 6 hours. The solvent was concentrated in vacuo and the reaction mixture was azeotroped with MeOH several times then placed on the high vacuum for 2 hours to dry to provide the desired 4-(dibenzylamino)benzoic acid which was confirmed by MS: cal'd 318.1 (MH+), exp 318.1 (MH+).

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. customthe reaction mixture was azeotroped with MeOH several times
  3. waitthen placed on the high vacuum for 2 hours
  4. customto dry

Sources & evidence

ORD record
ord-fd86ea3cea66472a851e288ca91a3bca
Source dataset
uspto-grants-2012_02
Patent number
US08119685B2

Reaction notes

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