Hydrochloric Acid → o-Chlorophenylacetic acid

HRID 2413349Notes

Reaction equation

HRID 2413349 reaction equation
C([CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15])[C:6](N)=[O:7])CCC.[OH-:16].[Na+].C(N)CCC.Cl>[Ni].O>[Cl:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:5][C:6]([OH:7])=[O:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8007ButylamineHCID 14798Sodium HydroxideHCID 86739887HCID 86739887, compound

Product 1

HCID 17124o-Chlorophenylacetic acidYield 95%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

225.5 g (1 mol) of N-t.-butyl-(2-chlorophenyl)-acetamide (melting point: 128°-130° C.) and 281 g of 15% strength NaOH (1.05 mols) are heated at 260° C., while stirring, for 3 hours in a 0.7 l nickel autoclave. The autoclave is cooled and the reaction mixture is run into a distillation apparatus. Distillation through a 30 cm column up to a head temperature of 100° C. gives 71.5 g of t.-butylamine of 97% purity, corresponding to a yield of 95% of the theoretical yield. 200 ml of water and 100 ml of 30% strength hydrochloric acid are added to the distillation bottom product. The acid which has been precipitated is filtered off with suction and dried in vacuo. 157.8 g of o-chlorophenylacetic acid of melting point 95° C. are obtained.

Workup

  1. temperatureThe autoclave is cooled
  2. distillationDistillation through a 30 cm column up to a head temperature of 100° C.
  3. customgives 71.5 g of t
  4. customThe acid which has been precipitated
  5. filtrationis filtered off with suction
  6. customdried in vacuo

Sources & evidence

ORD record
ord-a0d7333184654f28a7876d6f32d9a2f7
Source dataset
uspto-grants-1985_01
Patent number
US04496736

Reaction notes

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