Sulfuric Acid → Pentan-3-yl (2S)-2-hydroxypropanoate

HRID 2165288Notes

Reaction equation

HRID 2165288 reaction equation
[C:1]([OH:6])(=[O:5])[C@H:2]([CH3:4])[OH:3].[CH3:7][CH2:8][CH:9](O)[CH2:10][CH3:11].OS(O)(=O)=O>O>[C:1]([O:6][CH:9]([CH2:10][CH3:11])[CH2:8][CH3:7])(=[O:5])[C@H:2]([CH3:4])[OH:3]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 114283-PentanolHCID 107689L-Lactic Acid

Product 1

HCID 71429068Pentan-3-yl (2S)-2-hydroxypropanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 180 g of L-lactic acid, 528 g of 3-pentanol and 1 ml of conc. H2SO4 was refluxed in a Dean-Stark apparatus, until no more water formed (ca. 3 hours). The mixture was washed with water, NaHCO3 solution and brine, dried (MgSO4) and distilled to yield the title compound, boiling point 79°-81° C. at 15 mm of Hg.

Workup

  1. customformed (ca. 3 hours)
  2. washThe mixture was washed with water, NaHCO3 solution and brine
  3. dry with materialdried (MgSO4)
  4. distillationdistilled

Sources & evidence

ORD record
ord-4cf2697ba9554751b461d5dffb185dbe
Source dataset
uspto-grants-1990_07
Patent number
US04939253

Reaction notes

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