Methanol → methyl 3,3,3-trifluoro-dl-lactate

HRID 2419922Notes

Reaction equation

HRID 2419922 reaction equation
[OH:1][CH:2]([C:6]([F:9])([F:8])[F:7])[C:3]([OH:5])=[O:4].[CH3:10]O.S(=O)(=O)(O)O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O>[OH:1][CH:2]([C:6]([F:9])([F:8])[F:7])[C:3]([O:5][CH3:10])=[O:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 24436Sodium SulfateHCID 2448963,3,3-Trifluoro-2-hydroxypropanoic acid

Product 1

HCID 2760118methyl 3,3,3-trifluoro-dl-lactate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (±)-2-hydroxy-3,3,3-trifluoropropionic acid (7.8 g.), methanol (10 ml.) and concentrated sulphuric acid (0.5 ml.) is heated under reflux for 2 days. The cooled solution is poured into water (100 ml.), the mixture is saturated with sodium sulphate, and is extracted three times with ether. The extract is dried with sodium sulphate and evaporated. The residual oil (8.6 g.) is fractionally distilled to give (±)-methyl 2-hydroxy-3,3,3-trifluoropropionate b.p. 60°-64° C. at 12 mm. pressure, m.p. 50°-53° C. (3.9 g.).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 days
  3. extractionis extracted three times with ether
  4. dry with materialThe extract is dried with sodium sulphate
  5. customevaporated
  6. distillationThe residual oil (8.6 g.) is fractionally distilled

Sources & evidence

ORD record
ord-26dab223933647ae832c66895fe9d973
Source dataset
uspto-grants-1978_08
Patent number
US04107329

Reaction notes

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