Pyruvic Acid → HCID 21110707, compound

HRID 1766434Notes

Reaction equation

HRID 1766434 reaction equation
C1(C)C=CC=CC=1.[C:8]([OH:13])(=[O:12])[C:9]([CH3:11])=[O:10].[CH2:14]([O:16][CH2:17][CH2:18]O)[CH3:15]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[C:8]([O:13][CH2:15][CH2:14][O:16][CH2:17][CH3:18])(=[O:12])[C:9]([CH3:11])=[O:10]

Participants

6

Reactant 3

HCID 1060Pyruvic AcidHCID 1140TolueneHCID 8076Glycol monoethyl ether

Product 1

HCID 21110707HCID 21110707, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 962WaterSolvent

Procedure

A toluene solution (1 L) contaning pyruvic acid (440 g, 5.0 mol), 2-ethoxyethanol (450 g, 5.0 mol) and p-toluenesulfonic acid monohydrate (2.5 g) was heated and refluxed for 16 hours under nitrogen flow. The reaction led to generation of water in the system. However, the water was removed using Dean-Stark trap. The resultant reaction solution was cooled down to room temperature, followed by removal of toluene using an evaporator under a reduced pressure. The residual was then purified using reduced pressure distillation (40 mmHg, 100 to 105° C.) to give 2-ethoxyethyl pyruvate (544 g, yield: 68%).

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for 16 hours under nitrogen flow
  3. customHowever, the water was removed
  4. customThe resultant reaction solution
  5. customfollowed by removal of toluene using
  6. customan evaporator under a reduced pressure
  7. customThe residual was then purified
  8. distillationreduced pressure distillation (40 mmHg, 100 to 105° C.)

Sources & evidence

ORD record
ord-562298027613461e8e29ee782c108a8a
Source dataset
uspto-grants-2007_06
Patent number
US07230062B2

Reaction notes

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