Hydrochloric Acid → 4-(15-Methylhexadecyl)aminobenzoic acid

HRID 2163779

Reaction equation

HRID 2163779 reaction equation
[CH3:1][CH:2]([CH3:29])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]1[CH:28]=[CH:27][C:21]([C:22]([O:24]CC)=[O:23])=[CH:20][CH:19]=1.[OH-].[K+].C(O)C.Cl>O>[CH3:1][CH:2]([CH3:29])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 20437391Ethyl 4-(15-methylhexadecyl)aminobenzoate

Product 1

HCID 204373554-(15-Methylhexadecyl)aminobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3.5 g. of ethyl 4-(15-methylhexadecyl)aminobenzoate and 1.7 g. of 85% potassium hydroxide in 50 ml. of 95% ethanol is heated at reflux for 5 hours. The warm solution is diluted with 100 ml. water and adjusted to pH5 with 37% hydrochloric acid. The precipitate is collected, dried, and crystallized from acetic acid to yield the title compound as an amorphous, cream-colored solid.

Workup

  1. temperatureat reflux for 5 hours
  2. additionThe warm solution is diluted with 100 ml
  3. customThe precipitate is collected
  4. customdried
  5. customcrystallized from acetic acid

Sources & evidence

ORD record
ord-19b3502ac16c4938a3190be4e241db85
Source dataset
uspto-grants-1979_01
Patent number
US04136256

Linked notes

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