Chloroacetic Acid → (2,6-Dimethylphenoxy)acetic acid

HRID 1416558Notes

Reaction equation

HRID 1416558 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].Cl[CH2:11][C:12]([OH:14])=[O:13].[OH-].[Na+].C1(O)C=CC=CC=1>O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH2:11][C:12]([OH:14])=[O:13]

Participants

6

Reactant 4

HCID 300Chloroacetic Acid3×HCID 996PhenolHCID 113352,6-DimethylphenolHCID 14798Sodium Hydroxide3×

Product 1

HCID 101369(2,6-Dimethylphenoxy)acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

2,6-Dimethylphenol (102.8 g, 0.842 mol) and chloroacetic acid (159.6 g, 1.68 mol) in 1000 ml of H2O was added to a 3-L, 3-necked round bottom flask with mechanical stirring and a water-cooled condenser. A solution of NaOH (134.9 g, 3.37 mol) dissolved in 500 ml of water was slowly added to the above mixture via addition funnel and heat to reflux. After 2 hours, additional chloroacetic acid (79.4 g, 0.84 mol) and NaOH solution (67.2 g, 1.68 mol in in 200 ml water) was added to the reaction mixture. After 19 hours, additional chloroacetic acid (39.8 g, 0.42 mol) and NaOH solution (33.6 g, 0.84 mol in in 100 ml water) was added to the reaction mixture and refluxing was continued until starting phenol was consumed. The reaction flask was cooled in and ice-water bath and acidified to pH=1 with conc. HCl, causing a precipitate to form. The resulting slurry was stirred in the ice bath for 1 hour then filtered. The solid was dissolved in hot (100° C.) water and cooled to crystallize the product as white plates, mp=136-137° C., yield=78.8 g, 52%.

Workup

  1. additionwas slowly added to the above mixture via addition funnel
  2. temperatureheat to reflux
  3. waitAfter 19 hours
  4. temperaturerefluxing
  5. customwas consumed
  6. temperatureThe reaction flask was cooled in and ice-water bath
  7. customto form
  8. filtrationthen filtered
  9. dissolutionThe solid was dissolved in hot (100° C.) water
  10. temperaturecooled
  11. customto crystallize the product as white plates, mp=136-137° C., yield=78.8 g, 52%

Sources & evidence

ORD record
ord-a3750f1d57524eb483ae843ed5b88362
Source dataset
uspto-grants-1999_06
Patent number
US05914332

Reaction notes

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