1-Octanol → Octyl 2-oxopropanoate

HRID 1766432Notes

Reaction equation

HRID 1766432 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][CH3:21]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[C:8]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])(=[O:12])[C:9]([CH3:11])=[O:10]

Participants

6

Reactant 3

HCID 9571-OctanolHCID 1060Pyruvic AcidHCID 1140Toluene

Product 1

HCID 12422202Octyl 2-oxopropanoateYield 76.1%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 962WaterSolvent

Procedure

A toluene solution (1 L) containing pyruvic acid (440 g, 5.0 mol), n-octanol (651 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 (2 mmHg, 82 to 92° C.) to give octyl pyruvate (762 g, yield: 76%).

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 (2 mmHg, 82 to 92° C.)

Sources & evidence

ORD record
ord-4b26a830ad084533ad236a7c82d3a253
Source dataset
uspto-grants-2007_06
Patent number
US07230062B2

Reaction notes

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