Ethylene Glycol → 2-Hydroxyethyl phenoxyacetate

HRID 862796Notes

Reaction equation

HRID 862796 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.[CH2:12](O)[CH2:13][OH:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[O:1]([CH2:8][C:9]([O:11][CH2:12][CH2:13][OH:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 19188Phenoxyacetic Acid

Product 1

HCID 748042-Hydroxyethyl phenoxyacetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A 2-liter, 3-neck, round-bottom flask was equipped with a heating jacket, thermocouple and Dean-Stark apparatus for water removal. The flask was charged with 152 g (1.0 mole) phenoxyacetic acid, 62 g (1.0 mole) ethylene glycol, 22 g p-toluenesulfonic acid, 260 ml mixed xylenes and swept with nitrogen and sealed under a nitrogen balloon. The flask contents were heated to a pot temperature of 150° C. for 1/2 hour wherein 23 ml of water were collected and the reaction system cooled. Volatiles were removed at 110° C. in 4 mm of Hg vacuum to give a waxy white solid, IR shows formation of ester and disappearance of acid carbonyl, and mass spectrometry shows the molecular weight of 196.

Workup

  1. customsealed under a nitrogen balloon
  2. customwere collected
  3. temperaturethe reaction system cooled
  4. customVolatiles were removed at 110° C. in 4 mm of Hg vacuum
  5. customto give a waxy white solid, IR

Sources & evidence

ORD record
ord-65121cedff414b3c8f650fcaeba512c7
Source dataset
uspto-grants-1998_02
Patent number
US05719208

Reaction notes

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