Water → (2R)-2-Hydroxy-2,3,3-trimethylbutanoic acid

HRID 2396481Notes

Reaction equation

HRID 2396481 reaction equation
Cl([O-])=O.[Na+].S(=O)(=O)(O)N.[CH3:10][C@@:11]([OH:18])([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:12]=[O:13].[OH2:19]>O1CCCC1.O.C(Cl)Cl.CSC>[CH3:10][C@@:11]([OH:18])([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]([OH:19])=[O:13]

Participants

8

Reactant 4

HCID 962WaterHCID 5987Sulfamic AcidHCID 23668197Sodium ChloriteHCID 54105440HCID 54105440, compound

Product 1

HCID 13928263(2R)-2-Hydroxy-2,3,3-trimethylbutanoic acid

Reagents, catalysts & solvents 3

HCID 1068Dimethyl SulfideSolventHCID 6344DichloromethaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Sodium chlorite (1.81 g, 20 mmol) and sulfamic acid (1.94 g, 20 mmol) were added in succession to a stirred solution of (R)-2,3,3-trimethyl-2-hydroxybutanal (2.0 g, 15.4 mmol) in 30 ml of tetrahydrofuran-water (1:1) at 0° C. The mixture was allowed to warm to room temperature, stirred for 30 minutes, diluted with methylene chloride and about 1 ml of methyl sulfide was added followed by a small quantity of water. The organic layer was separated, the aqueous layer was extracted with methylene chloride, and the combined organic layer was dried (magnesium sulfate) and concentrated to afford a yellow gummy solid. Recrystallization from hexanes afford 1.45 g of (R) -2,3,3-trimethyl-2-hydroxybutanoic acid as a pale solid.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with methylene chloride
  4. dry with materialthe combined organic layer was dried (magnesium sulfate)
  5. concentrationconcentrated
  6. customto afford a yellow gummy solid
  7. customRecrystallization from hexanes

Sources & evidence

ORD record
ord-cd8bbd25c4fa4bf1bf58a92a0f43fd82
Source dataset
uspto-grants-1996_02
Patent number
US05492910

Reaction notes

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