Reaction #955954

ord-e3f4b785506842d7aa2cf4bb89d386b6

Reaction equation

CC(=O)C(=O)O
pyruvic acid
CCCCO
n-butanol
CCCCOC(=O)C(C)=O
butyl pyruvate
Yield 70.1%

Solvents

Conditions

Temperature
25°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturerefluxed for 16 hours
  2. 2
    Otherwhile removing water under a nitrogen gas stream, whereby a first reaction solution
  3. 3
    Otherwas obtained
  4. 4
    OtherThereafter, toluene was removed under reduced pressure (40 mmHg)
  5. 5
    Otheran evaporator
  6. 6
    workup.DISTILLATIONthe residue was purified by reduced pressure distillation (40 mmHg, 93 to 100° C.)

Procedure

First, a toluene (1 L) solution of pyruvic acid (440 g, 5.0 mol), n-butanol (371 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, whereby a first reaction solution was obtained. 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 (40 mmHg, 93 to 100° C.), whereby butyl pyruvate (505 g, yield 70%) was obtained.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08968975B2uspto-grants-2015_03