Hydrochloric Acid → 4-(11-Hydroxyundecylamino)benzoic acid

HRID 648306Notes

Reaction equation

HRID 648306 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[CH:24]=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][CH:15]=1.C(O)C.[OH-].[K+].Cl>O>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 20482494Ethyl 4-(11-hydroxyundecylamino)benzoate

Product 1

HCID 204825254-(11-Hydroxyundecylamino)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5 g. of ethyl 4-(11-hydroxyundecylamino)benzoate in 75 ml. 95% ethanol is saponified with 2.5 g. of 85% potassium hydroxide by refluxing for 5 hours. The warm solution is diluted with 150 ml. water and adjusted to pH 5 with 37% hydrochloric acid. The precipitate is filtered, washed with water, dried in vacuo and crystallized from acetic acid to yield 4-(11-hydroxyundecylamino)benzoic acid as a white solid.

Workup

  1. additionThe warm solution is diluted with 150 ml
  2. filtrationThe precipitate is filtered
  3. washwashed with water
  4. customdried in vacuo
  5. customcrystallized from acetic acid

Sources & evidence

ORD record
ord-1b008b60700646b0ab0d3e99c3ef19cb
Source dataset
uspto-grants-1983_10
Patent number
US04411903

Reaction notes

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