Lithium hydroxide, monohydrate → HCID 906624, compound

HRID 1489446Notes

Reaction equation

HRID 1489446 reaction equation
O.[OH-].[Li+].[C:4]1([C@H:10]2[O:16][C@H:11]2[C:12]([O:14]C)=[O:13])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O.CO>[C:4]1([C@H:10]2[O:16][C@H:11]2[C:12]([OH:14])=[O:13])[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 11789773HCID 11789773, compound

Product 1

HCID 906624HCID 906624, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Under ice cooling, a solution of 0.504 g of lithium hydroxide monohydrate dissolved in 25 ml of water was added dropwise to a solution of 1.78 g of methyl (2R,3R)-3-phenyl-2,3-epoxypropionate dissolved in 50 ml of methanol. The mixture was allowed to room temperature and stirred for 1 hour at the same temperature. Methanol was removed from the reaction mixture, and the pH of the residue was adjusted to 3 to 4 by adding a 5% aqueous citric acid solution thereto under ice cooling, and then extracted with chloroform. The chloroform layer was washed with brine and then dried over magnesium sulfate. The solvent was removed under reduced pressure, and hexane was added to the residue. Crystals precipitated were collected by filtration, washed with hexane and then dried to obtain 1.32 g of (2R,3R)-3-phenyl-2,3-epoxypropionic acid. Yield: 80%

Workup

  1. customwas allowed to room temperature
  2. customMethanol was removed from the reaction mixture
  3. additionby adding a 5% aqueous citric acid solution
  4. extractionunder ice cooling, and then extracted with chloroform
  5. washThe chloroform layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure, and hexane
  8. additionwas added to the residue
  9. customCrystals precipitated
  10. filtrationwere collected by filtration
  11. washwashed with hexane
  12. customdried

Sources & evidence

ORD record
ord-63f31d562fdb41f2b7cc2b69d4446f0b
Source dataset
uspto-grants-1997_10
Patent number
US05677470

Reaction notes

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