Butyric Acid → Lactic Acid

HRID 355102Notes

Reaction equation

HRID 355102 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:20]([O:23][CH:24]=[CH2:25])(=[O:22])[CH3:21].[C:26]([OH:31])(=[O:30])[CH2:27][CH2:28]C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:26]([OH:31])(=[O:30])[CH:27]([CH3:28])[OH:22].[C:20]([O:23][CH:24]=[CH2:25])(=[O:22])[CH3:21]

Participants

6

Reactant 3

HCID 264Butyric AcidHCID 7904Vinyl AcetateHCID 11776Triphenylphosphine

Product 2

HCID 612Lactic AcidHCID 7904Vinyl Acetate

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A 300 ml autoclave is charged with 0.692 g. of Pd(Ph3P)4 (0.6 mmole Pd), 3.15 g. of Ph3P (12 mmole), 83 ml of butyric acid as solvent, and 37 ml of vinyl acetate (0.4 mole). The autoclave was flushed, heated-up, and operated in a procedure similar to that described in Example 1. Several 1-ml increments of water were added, and then additional water to make a total of 9 ml. was added and the reaction continued overnight. After 23 hours of reaction time at 150° C. and 700 psig the reaction was terminated and analyzed by gas chromatography. The product mixture contained both 60-acetoxypropionic and lactic acids, the amount of lactic acid being 67-100% of the α-acetoxypropionic acid. The presence of lactic acid in this mixture was confirmed by nuclear magnetic resonance and mass spectroscopy. Thus lactic acid was produced in this experiment in one-step from vinyl acetate.

Workup

  1. additionA 300 ml autoclave is charged with 0.692 g
  2. customThe autoclave was flushed
  3. temperatureheated-up
  4. additionSeveral 1-ml increments of water were added
  5. additionwas added
  6. customthe reaction continued overnight
  7. customAfter 23 hours of reaction time at 150° C.
  8. custom700 psig the reaction was terminated

Sources & evidence

ORD record
ord-88784e45283e411ea45ea4a0daf1fc13
Source dataset
uspto-grants-1983_03
Patent number
US04377708

Reaction notes

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