Acetyl chloride → (2R)-2-methyl-3-acetyloxypropionic acid

HRID 1670006Notes

Reaction equation

HRID 1670006 reaction equation
[CH3:1][C@H:2]([CH2:6][OH:7])[C:3]([OH:5])=[O:4].[C:8](Cl)(=[O:10])[CH3:9]>N1C=CC=CC=1>[CH3:1][C@H:2]([CH2:6][O:7][C:8](=[O:10])[CH3:9])[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 11217234(2R)-3-hydroxy-2-methylpropanoic acid

Product 1

HCID 12997379(2R)-2-methyl-3-acetyloxypropionic acidYield 520%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (2R)-2-methyl-3-hydroxypropionic acid (10.0 g, 100 mmol) in pyridine (30 mL) as added acetyl chloride(11.8 g, 15.0 mmol) at 0° C., and the reaction mixture was warmed to rt. After being stirried for 3 h, the reaction mixture was quenched with 1N HCl (30 mL), and the pH of the solution was adjusted to 3-4. The organic material was extracted with EtOAc, and the extracts were washed with 1N HCl at 4-5 times, dried over MgSO4, filtered, and concentrated to give the title compound (11.4 g, 95.0%).

Workup

  1. customthe reaction mixture was quenched with 1N HCl (30 mL)
  2. extractionThe organic material was extracted with EtOAc
  3. washthe extracts were washed with 1N HCl at 4-5 times
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e9485b3326bd4c9194d0de7a2659e7e2
Source dataset
uspto-grants-2011_08
Patent number
US07989634B2

Reaction notes

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