Hydrochloric Acid → HCID 15450552, compound

HRID 1107393Notes

Reaction equation

HRID 1107393 reaction equation
[OH:1][C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH:6]([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4].[OH-].[K+].[CH2:17](I)[CH3:18].Cl>CS(C)=O.O>[CH2:17]([O:1][C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH:6]([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4])[CH3:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 14797Potassium HydroxideHCID 122966392-Hydroxy-3-methyl-2-phenylbutanoic acid2×

Product 1

HCID 15450552HCID 15450552, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 2-hydroxy-3-methyl-2-phenylbutanoic acid (Compound (5), 30.0 g) in dimethyl sulfoxide (250 ml) was added 85% powdered potassium hydroxide (60 g) and the mixed solution was stirred for one hour. Under ice cooling, ethyl iodide (55 ml) was added and the resulting mixture was stirred at room temperature for 3 days. After the addition of water (100 ml), the resulting mixture was stirred at 80° C. for 6 hours. The reaction mixture was acidified with 1N hydrochloric acid, followed by extraction with ether. The ether layer was dried over anhydrous sodium sulfate and removed under reduced pressure. To the residue, hexane (200 ml) was added. After the resulting mixture was allowed to stand overnight, the crystals so precipitated were removed by filtration. The filtrate was removed under reduced pressure to obtain the title compound (27.0 g, 78.7%) as an oil.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 3 days
  2. stirringthe resulting mixture was stirred at 80° C. for 6 hours
  3. extractionfollowed by extraction with ether
  4. dry with materialThe ether layer was dried over anhydrous sodium sulfate
  5. customremoved under reduced pressure
  6. additionTo the residue, hexane (200 ml) was added
  7. waitto stand overnight
  8. customthe crystals so precipitated
  9. customwere removed by filtration
  10. customThe filtrate was removed under reduced pressure

Sources & evidence

ORD record
ord-6256b498b45b46ce90997be748c12be9
Source dataset
uspto-grants-2000_05
Patent number
US06060485

Reaction notes

Loading…