Chloroacetic Acid → (2-Phenylethoxy)acetic acid

HRID 1905962Notes

Reaction equation

HRID 1905962 reaction equation
[CH2:1]([OH:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].[Na+].Cl[CH2:13][C:14]([OH:16])=[O:15]>CN(C)C=O>[C:3]1([CH2:2][CH2:1][O:9][CH2:13][C:14]([OH:16])=[O:15])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 60542-PhenylethanolHCID 24758Sodium hydride

Product 1

HCID 13208922(2-Phenylethoxy)acetic acidYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

6.1 g of phenethyl alcohol in 100 ml of dimethylformamide were treated with 4.8 g of a 50% sodium hydride dispersion in mineral oil and the mixture was stirred for 10 minutes at 60° C. 4.73 g of chloroacetic acid were added and the mixture was heated at 60° C. for 0.5 hour with stirring. The mixture was evaporated to dryness and the residue was partitioned between water and diethyl ether. The aqueous phase was acidified to pH 1 with concentrated hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water, dried over sodium sulfate, filtered and evaporated to dryness. The residue was recrystallized from ethyl acetate/hexane to give 7.65 g (85%) of 2-phenylethoxyacetic acid of melting point 46°-48° C.

Workup

  1. temperaturethe mixture was heated at 60° C. for 0.5 hour
  2. stirringwith stirring
  3. customThe mixture was evaporated to dryness
  4. customthe residue was partitioned between water and diethyl ether
  5. extractionextracted with ethyl acetate
  6. washThe organic phase was washed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-166cf7c0ec044f669e0df825aaa7b893
Source dataset
uspto-grants-1987_03
Patent number
US04649160

Reaction notes

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