Chloroacetic Acid → 2-(4-Methylthiophenyl)ethoxyacetic acid

HRID 1905971Notes

Reaction equation

HRID 1905971 reaction equation
[CH3:1][S:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8][OH:9])=[CH:5][CH:4]=1.[H-].[Na+].Cl[CH2:15][C:16]([OH:18])=[O:17].O>CS(C)=O>[CH3:1][S:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8][O:9][CH2:15][C:16]([OH:18])=[O:17])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 300Chloroacetic AcidHCID 962WaterHCID 24758Sodium hydrideHCID 27600862-(4-Methylsulfanylphenyl)ethanol

Product 1

HCID 132089272-(4-Methylthiophenyl)ethoxyacetic acidYield 46.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

6.27 g of 4-methylthiophenethyl alcohol in 100 ml of dimethyl sulfoxide were treated with 3.58 g of a 50% sodium hydride dispersion in mineral oil and the mixture was stirred at 60° C. for 10 minutes. 3.53 g of chloroacetic acid were added and the heating was continued at 80° C. for 3 hours while stirring. The mixture was cooled, poured into water and washed with ethyl acetate. The aqueous phase was acidified to pH 1 with concentrated hydrochloric acid and extracted with ethyl acetate. The organic phase was separated, washed well with water, dried over sodium sulfate, filtered and evaporated to dryness. The residue was recrystallized from toluene/hexane to give 3.89 g (46%) of 2-(4-methylthiophenyl)ethoxyacetic acid of melting 58°-60° C.

Workup

  1. waitthe heating was continued at 80° C. for 3 hours
  2. stirringwhile stirring
  3. temperatureThe mixture was cooled
  4. washwashed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. customThe organic phase was separated
  7. washwashed well with water
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customThe residue was recrystallized from toluene/hexane

Sources & evidence

ORD record
ord-7546e7c372a341e78972a311d7b7679b
Source dataset
uspto-grants-1987_03
Patent number
US04649160

Reaction notes

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