Hydrochloric Acid → 4-(13,13-Dimethyltetradecyl)aminobenzoic acid

HRID 1980186Notes

Reaction equation

HRID 1980186 reaction equation
[CH3:1][C:2]([CH3:28])([CH3:27])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22]CC)=[O:21])=[CH:18][CH:17]=1.C(O)C.[OH-].[K+].Cl>O>[CH3:1][C:2]([CH3:28])([CH3:27])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 20437372Ethyl 4-(13,13-dimethyltetradecyl)aminobenzoate

Product 1

HCID 204373434-(13,13-Dimethyltetradecyl)aminobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5 g. of ethyl 4-(13,13-dimethyltetradecyl)aminobenzoate 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 the title compound as a cream-colored, amorphous 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-6c68aef8b29c40c5bc1a92723d9a1c06
Source dataset
uspto-grants-1984_11
Patent number
US04485105

Reaction notes

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