Hydrochloric Acid → 4-Chloro-2-[2-(dimethylamino)-2-oxoethoxy]benzoic acid

HRID 412009Notes

Reaction equation

HRID 412009 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([O:8]CC(N(C)C)=O)=[O:7])=[C:4]([O:17][CH2:18][C:19]([N:21]([CH3:23])[CH3:22])=[O:20])[CH:3]=1.CO.O.[OH-].[Li+].Cl>O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:17][CH2:18][C:19]([N:21]([CH3:23])[CH3:22])=[O:20])[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 223224322-(Dimethylamino)-2-oxoethyl 4-chloro-2-(2-(dimethylamino)-2-oxoethoxy)benzoate

Product 1

HCID 112539014-Chloro-2-[2-(dimethylamino)-2-oxoethoxy]benzoic acidYield 159.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from step (a) (1.0 g) was dissolved in a 2:1 water:methanol mixture (15 ml) and lithium hydroxide monohydrate added. After 2 hours 2M aqueous hydrochloric acid and ethyl acetate were added, the organic phase separated, dried and concentrated to give the product as a solid (1.2 g), m.p. 141-142° C.

Workup

  1. customthe organic phase separated
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-60dc0773101b4cd5beef22450cb88743
Source dataset
uspto-grants-2003_05
Patent number
US06562825B1

Reaction notes

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