Phenol → Acetic acid, 2-phenoxy-, ethyl ester

HRID 1761274Notes

Reaction equation

HRID 1761274 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[I-].[Na+].Cl[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].CC1C=C(OC)C=CC=1>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[O:7]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 996PhenolHCID 5238Sodium IodideHCID 75303-MethoxytolueneHCID 7751Ethyl chloroacetateHCID 14798Sodium Hydroxide

Product 1

HCID 17365Acetic acid, 2-phenoxy-, ethyl ester

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent2×

Procedure

The three-necked 500 mL flask was filled with phenol (1.89 g, 20 millimoles, Aldrich, 99+%), sodium hydroxide (1.76 g, 50% w/w solution in water, 22 millimoles, Aldrich), sodium iodide (0.18 g, 1 millimole, Aldrich, 98%), and water (196.78 g) and immersed in the water bath kept at 60° C. The excess molar concentration of sodium hydroxide was 0.10. The mixture was stirred mechanically at 600 rpm. Next, the organic phase consisting of ethyl chloroacetate (9.84 g, 80 millimoles, Aldrich, 99%), Aliquat 336 (0.834 g, 2 millimoles, and 3-methylanisole (GC standard, 0.490 g, 4 millimoles, Aldrich, 99%) was introduced into the flask. The organic phase: aqueous phase weight ratio was 1:18. The stirring was continued at 60° C. for several hours. The aliquots were taken every 60-90 minutes and briefly centrifuged. The organic phase was injected into the GC instrument. The yield of ethyl phnoxyacetate after 390 minutes retention time was 18%.

Workup

  1. customkept at 60° C
  2. concentrationThe excess molar concentration of sodium hydroxide
  3. additionwas introduced into the flask
  4. waitThe stirring was continued at 60° C. for several hours
  5. waitThe yield of ethyl phnoxyacetate after 390 minutes retention time was 18%

Sources & evidence

ORD record
ord-60c30701bc754283ac26758696254b32
Source dataset
uspto-grants-2005_01
Patent number
US06846946B2

Reaction notes

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