Pyruvic Acid → HCID 21110708, compound

HRID 1766433Notes

Reaction equation

HRID 1766433 reaction equation
C1(C)C=CC=CC=1.[C:8]([OH:13])(=[O:12])[C:9]([CH3:11])=[O:10].[CH2:14](O)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[C:8]([O:13][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14])(=[O:12])[C:9]([CH3:11])=[O:10]

Participants

6

Reactant 3

HCID 1060Pyruvic AcidHCID 1140TolueneHCID 8221Stearyl Alcohol

Product 1

HCID 21110708HCID 21110708, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 962WaterSolvent

Procedure

A toluene solution (1 L) containing pyruvic acid (220 g, 2.5 mol), stearyl alcohol (675 g, 2.5 mol) and p-toluenesulfonic acid monohydrate (1.2 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 (1 mmHg, 110 to 120° C.) to give stearyl pyruvate (512 g, yield: 80%).

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 (1 mmHg, 110 to 120° C.)

Sources & evidence

ORD record
ord-6b85526102664312ad5452bbb47d992c
Source dataset
uspto-grants-2007_06
Patent number
US07230062B2

Reaction notes

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