Hydrochloric Acid → Benzoic Acid

HRID 27461

Reaction equation

HRID 27461 reaction equation
NCC[C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1.[Na].C([O-])(=O)C.[Na+].C(NCCC1C=CC(C(O)=O)=CC=1)(=O)C.[OH-].[Na+].ClC1C=C(C=CC=1)CCl.Cl>O.CC(C)=O>[C:8]([OH:10])(=[O:9])[C:7]1[CH:11]=[CH:12][CH:4]=[CH:5][CH:6]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 12103m,alpha-DichlorotolueneHCID 14798Sodium HydroxideHCID 3437014-(2-Acetamidoethyl)benzoic acidHCID 517045Sodium AcetateHCID 705908304-(2-Aminoethyl)-benzoic acid sodium

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

50 ml of a 1-molar solution of 4-(2-aminoethyl)-benzoic acid-sodium, which contained, in addition, 0.05 mole of sodium acetate and which had been prepared by saponification of 4-(2-acetylaminoethyl)-benzoic acid with sodium hydroxide solution, was combined with 50 ml of acetone and then with the solution of 9 g of 3-chlorobenzyl chloride in a small amount of acetone. The whole was stirred for about 1 hour, water and hydrochloric acid were added, filtered off with suction and the product was recrystallized from a mixture of water and isopropanol. The 4-(2-<3-chloro-benzamido>-ethyl)-benzoic acid obtained was found to melt at 200° to 202° C.

Workup

  1. filtrationfiltered off with suction
  2. customthe product was recrystallized from a mixture of water and isopropanol

Sources & evidence

ORD record
ord-9025e657a2784680af368ace6a1095ec
Source dataset
uspto-grants-1980_09
Patent number
US04221815

Linked notes

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