Hydrochloric Acid → 5-Chloro-o-anisic acid

HRID 27465

Reaction equation

HRID 27465 reaction equation
Cl.[OH-:2].[Na+].[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([O:14][CH3:15])=[C:9]([CH:13]=1)[C:10](Cl)=[O:11]>CC(C)=O.O>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([O:14][CH3:15])=[C:9]([CH:13]=1)[C:10]([OH:2])=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 123841765-Chloro-2-methoxybenzoyl chloride

Product 1

HCID 769705-Chloro-o-anisic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent2×

Procedure

2.5 g of hydrochloride were dissolved in 25 ml of acetone and 0.8 g of NaOH in 20 ml of water. To this solution, there were added 2 g of 5-chloro-2-methoxy-benzoyl chloride in 20 ml of acetone and the whole was stirred for 1 hour. Then, water and dilute hydrochloric acid were added and the product was recrystallized from methanol. The 4-(2-<5-chloro-2-methoxy-benzamido>-ethyl)-5-chloro-2-methoxy-benzoic acid so obtained was found to melt at 171°-173° C.

Workup

  1. customthe product was recrystallized from methanol

Sources & evidence

ORD record
ord-7c74eb287f1e4f3aa2f705a2242fad10
Source dataset
uspto-grants-1980_09
Patent number
US04221815

Linked notes

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