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

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[Li].O.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

Reactant 4

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 168937Lithium hydroxide, monohydrate

HCID 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

Procedure

The product from step (v) (1.0 g) was dissolved in a 2:1 water: methanol mixture (15 ml) and LiOH.H2O added. After 2 hours 2M aqueous HCl solution and ethyl acetate were added, the organic phase separated, dried and concentrated to give the sub-titled product as a solid (1.2 g).