5-Chloro-2-ethoxybenzoyl chloride → Benzoic Acid

HRID 27463Notes

Reaction equation

HRID 27463 reaction equation
Cl.NCC[C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1.C(OC1C=CC(Cl)=CC=1C(Cl)=O)C>[OH-].[Na+].CC(C)=O.O>[C:9]([OH:11])(=[O:10])[C:8]1[CH:12]=[CH:13][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 128632345-Chloro-2-ethoxybenzoyl chlorideHCID 162179904-(2-Aminoethyl)benzoic acid hydrochloride

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

10 g of 4-(2-aminoethyl)-benzoic acid hydrochloride were dissolved in 60 ml of 2 N-sodium hydroxide solution and, after addition of 75 ml of acetone, a solution of 11 g of 2-ethoxy-5-chloro-benzoylchloride in 20 ml of acetone was added dropwise, while stirring. Stirring was continued for 2 hours, the mixture was diluted with water, filtered and acidified with dilute hydrochloric acid. After filtration with suction, the product was recrystallized from ethanol. The 4-(2-<2-ethoxy-5-chloro-benzamido>-ethyl)-benzoic acid obtained was found to melt at 180° C.

Workup

  1. stirringStirring
  2. filtrationfiltered
  3. filtrationAfter filtration with suction
  4. customthe product was recrystallized from ethanol

Sources & evidence

ORD record
ord-9ea65976033349a791ade5e6d989ca8d
Source dataset
uspto-grants-1980_09
Patent number
US04221815

Reaction notes

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