Sodium Hydroxide → HCID 22105629, compound

HRID 1455938Notes

Reaction equation

HRID 1455938 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]1[CH:30]=[CH:29][CH:28]=[CH:27][C:12]=1[CH2:13][N:14]([C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=1)[CH2:15][CH3:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO.O1CCCC1>[CH2:3]([O:10][C:11]1[CH:30]=[CH:29][CH:28]=[CH:27][C:12]=1[CH2:13][N:14]([C:17]1[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:25][CH:26]=1)[CH2:15][CH3:16])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22105545HCID 22105545, compound

Product 1

HCID 22105629HCID 22105629, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

40% Aqueous sodium hydroxide (100 mL) was added to a solution of methyl 4-[N-(2-benzyloxybenzyl)-N-ethylamino]benzoate (44.0 g) in a mixture of methanol (200 mL) and tetrahydrofuran (100 mL) and the resulting mixture was heated under reflux for 6 hours. The reaction mixture was reduced to half its volume on a rotary evaporator and water (300 mL) was added. The mixture was acidified with acetic acid, the precipitate was filtered, washed three times with diethyl ether (50 mL each time) and dried in a vacuum oven at 60° C. to give 4-[N-(2-benzyloxybenzyl)-N-ethylamino]benzoic acid, melting point 165° C., yield 38.0 g (89%).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 6 hours
  3. customThe reaction mixture was reduced to half its volume on a rotary evaporator and water (300 mL)
  4. additionwas added
  5. filtrationthe precipitate was filtered
  6. washwashed three times with diethyl ether (50 mL each time)
  7. customdried in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-6396b7a268a54768a559ede55428dc8f
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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