Hydrochloric Acid → 4-({[4-(Benzyloxy)phenyl]methyl}amino)benzoic acid

HRID 2052485Notes

Reaction equation

HRID 2052485 reaction equation
[CH2:1]([O:8][C:9]1[CH:27]=[CH:26][C:12]([CH2:13][NH:14][C:15]2[CH:25]=[CH:24][C:18]([C:19]([O:21]CC)=[O:20])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl>C(O)C.O>[CH2:1]([O:8][C:9]1[CH:27]=[CH:26][C:12]([CH2:13][NH:14][C:15]2[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:24][CH:25]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13079673Ethyl 4-({[4-(benzyloxy)phenyl]methyl}amino)benzoate

Product 1

HCID 130796724-({[4-(Benzyloxy)phenyl]methyl}amino)benzoic acid

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of 10 g. of ethyl p-[p-(benzyloxy)benzylamino]benzoate (prepared as described in Example 11) 10 g. of potassium hydroxide and 200 ml. of ethanol-water (9:1) are refluxed for 4.5 hours. While hot, the mixture is acidified with concentrated hydrochloric acid. Dilution with water and filtration gives tan crystals which are recrystallized from glacial acetic acid to give off-white crystals, m.p. 206°-208° C.

Workup

  1. additionA mixture of 10 g
  2. filtrationDilution with water and filtration
  3. customgives tan crystals which
  4. customare recrystallized from glacial acetic acid
  5. customto give off-white crystals, m.p. 206°-208° C.

Sources & evidence

ORD record
ord-c8ad0d790e8f408a9a811561f269b2d0
Source dataset
uspto-grants-1980_01
Patent number
US04185115

Reaction notes

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