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

HRID 1106147Notes

Reaction equation

HRID 1106147 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-06cb83b35ac84943b7fbee6e7aa7a1b9
Source dataset
uspto-grants-1982_01
Patent number
US04311846

Reaction notes

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