1-Butanol → Butyl pyruvate

HRID 868772

Reaction equation

HRID 868772 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[O:3].[CH2:7](O)[CH2:8][CH2:9][CH3:10]>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][CH3:10])(=[O:5])[C:2]([CH3:4])=[O:3]

Participants

5

Reactant 2

HCID 2631-ButanolHCID 1060Pyruvic Acid

Product 1

HCID 523883Butyl pyruvateYield 70.1%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
25 °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.

Workup

  1. temperaturerefluxed for 16 hours
  2. customwhile removing water under a nitrogen gas stream, whereby a first reaction solution
  3. customwas obtained
  4. customThereafter, toluene was removed under reduced pressure (40 mmHg)
  5. customan evaporator
  6. distillationthe residue was purified by reduced pressure distillation (40 mmHg, 93 to 100° C.)

Sources & evidence

ORD record
ord-e3f4b785506842d7aa2cf4bb89d386b6
Source dataset
uspto-grants-2015_03
Patent number
US08968975B2

Linked notes

Loading…