Ethylene Glycol → 2-Hydroxyethyl phenoxyacetate

HRID 1105775Notes

Reaction equation

HRID 1105775 reaction equation
[O:1]([CH2:8][C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC=CC=1.[CH2:18](O)[CH2:19][OH:20]>C1(C)C(S(O)(=O)=O)=CC=CC=1.O>[O:1]([CH2:8][C:9]([O:11][CH2:18][CH2:19][OH:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 241BenzeneHCID 19188Phenoxyacetic Acid

Product 1

HCID 748042-Hydroxyethyl phenoxyacetate

Reagents, catalysts & solvents 2

HCID 69252-Methylbenzenesulfonic acidCatalystHCID 962WaterSolvent

Procedure

Into a 5000 ml. 3-necked flask, equipped with thermometer, stirrer, condenser and Dean-Stark trap were weighed 924 gms. of phenoxyacetic acid. There were added 2 gms. toluene sulfonic acid as catalyst and 100 mls. of benzene. Heating was started with stirring and there were added 2270 gms. of ethylene glycol. At reflux temperature water was collected and taken off. After 11 and 1/2 hours of refluxing the reaction mixture was transferred to a 6 liter separatory funnel where excess ethylene glycol was separated and recovered. The benzene layer was extracted with hot water and sodium bicarbonate and the benzene layer was filtered warm through a molecular sieve to remove residual water. The benzene extract was allowed to stand overnight and the crystals which formed were removed by filtration and dried in a vacuum oven. A total of 370.2 gms. product was recovered, m.p. 61°-63° C.

Workup

  1. custom3-necked flask, equipped with thermometer, stirrer, condenser and Dean-Stark trap
  2. additionThere were added 2 gms
  3. temperatureHeating
  4. additionthere were added 2270 gms
  5. customwas collected
  6. temperatureAfter 11 and 1/2 hours of refluxing the reaction mixture
  7. customwas transferred to a 6 liter separatory funnel
  8. customwhere excess ethylene glycol was separated
  9. customrecovered
  10. extractionThe benzene layer was extracted with hot water and sodium bicarbonate
  11. filtrationthe benzene layer was filtered
  12. temperaturewarm through a molecular sieve
  13. customto remove residual water
  14. extractionThe benzene extract
  15. customthe crystals which formed
  16. customwere removed by filtration
  17. customdried in a vacuum oven
  18. customproduct was recovered

Sources & evidence

ORD record
ord-becefad6fd9e42958309278f1c4b7628
Source dataset
uspto-grants-1982_01
Patent number
US04310512

Reaction notes

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