Lactic Acid → Poly[oxy[(1S)-1-methyl-2-oxo-1,2-ethanediyl]], α-hydro-ω-(2-propyn-1-yloxy)-

HRID 2275980Notes

Reaction equation

HRID 2275980 reaction equation
[OH:1][CH:2]([CH3:6])[C:3]([OH:5])=[O:4].[CH2:7](O)[C:8]#[CH:9].S(=O)(=O)(O)O.C([O-])(=O)C.[Na+]>C1(C)C=CC=CC=1>[OH:1][CH:2]([CH3:6])[C:3]([O:5][CH2:9][C:8]#[CH:7])=[O:4]

Participants

6

Reactant 4

HCID 612Lactic AcidHCID 1118Sulfuric AcidHCID 7859Propargyl alcoholHCID 517045Sodium Acetate

Product 1

HCID 86651912Poly[oxy[(1S)-1-methyl-2-oxo-1,2-ethanediyl]], α-hydro-ω-(2-propyn-1-yloxy)-Yield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

52.99 g (0.50 mol) of an aqueous solution of 85% 2-hydroxypropionic acid and 45 mL of toluene were dissolved in 84.09 g (1.50 mol) of propargyl alcohol, and 1.0 mL of concentrated sulfuric acid was added thereto. Using a Dean-Stark device under normal pressure, the formed water was removed from the system, and this was further reacted under reflux under normal pressure. After 3 hours, the reaction liquid was analyzed through liquid chromatography, and the disappearance of the starting materials was confirmed. Then, the reaction liquid was neutralized with sodium acetate added thereto, filtered, and the filtrate was concentrated. The residue was purified through reduced pressure distillation to give 28.81 g (45% yield) of 2-propynyl 2-hydroxypropionate.

Workup

  1. customthe formed water was removed from the system
  2. customthis was further reacted
  3. temperatureunder reflux under normal pressure
  4. customthe reaction liquid
  5. customThen, the reaction liquid
  6. additionadded
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. distillationThe residue was purified through reduced pressure distillation

Sources & evidence

ORD record
ord-c9cc4ff08c464414ae357555e93d2f90
Source dataset
uspto-grants-2015_09
Patent number
US09130244B2

Reaction notes

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