1-Octanol → Octyl 2-oxopropanoate

HRID 868774Notes

Reaction equation

HRID 868774 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[O:3].[CH2:7](O)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[C:1]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])(=[O:5])[C:2]([CH3:4])=[O:3]

Participants

5

Reactant 2

HCID 9571-OctanolHCID 1060Pyruvic Acid

Product 1

HCID 12422202Octyl 2-oxopropanoateYield 76.1%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

A toluene (1 L) solution of 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 while removing water under a nitrogen gas stream, thereby obtaining a first reaction solution. Next, the first reaction solution was cooled to room temperature (25° C.). Thereafter, toluene was removed under reduced pressure (40 mmHg) using an evaporator, and the residue was purified by reduced pressure distillation (2 mmHg, 82 to 92° C.), thereby obtaining octyl pyruvate (762 g, yield 76%).

Workup

  1. temperaturerefluxed for 16 hours
  2. customwhile removing water under a nitrogen gas stream
  3. customobtaining a first reaction solution
  4. customThereafter, toluene was removed under reduced pressure (40 mmHg)
  5. customan evaporator
  6. distillationthe residue was purified by reduced pressure distillation (2 mmHg, 82 to 92° C.)

Sources & evidence

ORD record
ord-30fdd1b542004ea68696608a9ee49c06
Source dataset
uspto-grants-2015_03
Patent number
US08968975B2

Reaction notes

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