Acetic Acid → 2-Acetoxypropionic Acid

HRID 337004

Reaction equation

HRID 337004 reaction equation
[OH:1][CH:2]([CH3:6])[C:3]([OH:5])=[O:4].S(=O)(=O)(O)O.[C:12](O)(=[O:14])[CH3:13]>C1(C)C=CC=CC=1>[C:12]([O:1][CH:2]([CH3:6])[C:3]([OH:5])=[O:4])(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 612Lactic AcidHCID 1118Sulfuric Acid

Product 1

HCID 790412-Acetoxypropionic AcidYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Reflux a mixture of 2-hydroxy-propionic acid (480 ml, 85% in water) and sulfuric acid (2 mL) in acetic acid (2500 mL) and toluene (300 mL) for overnight. After removal of solvent under vacuum, purify the residue by distillation to give 2-acetoxy-propionic acid (550 g, 92%) as colorless oil. 1H NMR (CDCl3, 400 MHz): δ 9.27 (brs, 1H), 5.10 (m, 1H), 2.13 (s, 3H), 1.53 (d, J=7.2, 3H).

Workup

  1. temperatureReflux
  2. customAfter removal of solvent under vacuum
  3. custompurify the residue
  4. distillationby distillation

Sources & evidence

ORD record
ord-279584c9e6454c1ea437162fa13ef2eb
Source dataset
uspto-grants-2014_11
Patent number
US08889710B2

Linked notes

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