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

HRID 1703080Notes

Reaction equation

HRID 1703080 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-12397f677470406295a1c14bbe0cc084
Source dataset
uspto-grants-1982_09
Patent number
US04350822

Reaction notes

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