Hydrochloric Acid → HCID 22723506, compound

HRID 1581829Notes

Reaction equation

HRID 1581829 reaction equation
[C:1]([C:3]([CH3:11])([CH3:10])[CH:4]([OH:9])[CH2:5][C:6]([OH:8])=[O:7])#[N:2].[C:12](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.Cl>CN(C=O)C.C1(C)C=CC=CC=1>[C:1]([C:3]([CH3:11])([CH3:10])[CH:4]([OH:9])[CH2:5][C:6]([O:8][CH3:12])=[O:7])#[N:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 22723509HCID 22723509, compound

Product 1

HCID 22723506HCID 22723506, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

4-Cyano-3-hydroxy-4-methylpentanoic acid (7.7 g, 49 mmol) was dissolved in DMF (50 mL) and potassium carbonate (10.16 g, 73.5 mmol) was added. Dimethyl sulfate (8.03 g, 63.7 mmol) was dropwise added with vigorous stirring. The mixture was stirred at room temperature for 2 hr and toluene (50 mL) was added. 2N Aqueous hydrochloric acid solution (40 mL, 80 mmol) was dropwise added with vigorous stirring. After partitioning, a toluene layer was separated and an aqueous layer was extracted again with toluene (25 mL). The toluene layers were combined and concentrated under reduced pressure to give methyl 4-cyano-3-hydroxy-4-methylpentanoate (7.13 g, 41.6 mmol). The yield was 85% relative to 4-cyano-3-hydroxy-4-methylpentanoic acid.

Workup

  1. customAfter partitioning
  2. customa toluene layer was separated
  3. extractionan aqueous layer was extracted again with toluene (25 mL)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-541004e693814f06af8e3b8e91cc1a66
Source dataset
uspto-grants-2004_05
Patent number
US06730803B2

Reaction notes

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