Hydrochloric Acid → 4-(15-Carboxypentadecylamino)benzoic acid

HRID 904243Notes

Reaction equation

HRID 904243 reaction equation
[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]1[CH:31]=[CH:30][C:24]([C:25]([O:27]CC)=[O:26])=[CH:23][CH:22]=1)([O:3]C)=[O:2].[OH-].[K+].C(O)C.Cl>O>[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[CH:30][CH:31]=1)([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 21163354Ethyl 4-(15-carbomethoxypentadecylamino)benzoate

Product 1

HCID 102952934-(15-Carboxypentadecylamino)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 8.8 g. of ethyl 4-(15-carbomethoxypentadecylamino)benzoate, 4.5 g. of potassium hydroxide, and 10 ml. of water in 90 ml. of ethanol is stirred at 75° for 10 hours, cooled, diluted with water, brought to pH 4 with dilute hydrochloric acid, and filtered. The solid is dried and crystallized from acetic acid to yield 4-(15-carboxypentadecylamino)benzoic acid as a white crystalline solid.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. customThe solid is dried
  4. customcrystallized from acetic acid

Sources & evidence

ORD record
ord-168153b1b0424573b1fb911b2e34ea8e
Source dataset
uspto-grants-1980_10
Patent number
US04230628

Reaction notes

Loading…