Chloroacetic Acid → 2-(4-Chloro-2-methoxyphenoxy)acetic acid

HRID 11613

Reaction equation

HRID 11613 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([O:11][CH3:12])[CH:5]=1.Cl[CH2:14][C:15]([OH:17])=[O:16].Cl>O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:14][C:15]([OH:17])=[O:16])=[C:6]([O:11][CH3:12])[CH:5]=1

Participants

6

Reactant 4

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 280504-Chloroguaiacol

Product 1

HCID 116585842-(4-Chloro-2-methoxyphenoxy)acetic acidYield 120%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of sodium hydroxide (6.6 g, 160 mmol) in water (45 mL) was added 4-chloro-2-methoxy-phenol (2.0 mL, 16 mmol) and chloroacetic acid (7.7 g, 81 mmol). The resulting mixture was heated to 95° C. and stirred for three hours. The reaction was allowed to cool to ambient temperature and slowly acidified with concentrated hydrochloric acid (10 mL) until the mixture became a solution and then extracted with diethyl ether. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to give the title compound (4.16 g).

Workup

  1. temperatureto cool to ambient temperature
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b437499df33d48f784286683f8fd74db
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Linked notes

Loading…