Isovaleric Acid → Chloromethyl 3-methylbutanoate

HRID 1419462Notes

Reaction equation

HRID 1419462 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4].C([O-])(O)=O.[Na+].[Cl:13][CH2:14]OS(Cl)(=O)=O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O.ClCCl>[C:1]([O:7][CH2:14][Cl:13])(=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

7

Reactant 3

HCID 10430Isovaleric AcidHCID 516892Sodium BicarbonateHCID 2733556Chloromethyl chlorosulfate

Product 1

HCID 534383Chloromethyl 3-methylbutanoateYield 61.1%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1.532 g of isovaleric acid (1), 5.04 g of NaHCO3 and 0.518 g of tetrabutylammonium hydrogen sulfate were dissolved in a mixture solution of 50 ml of water and 50 ml of dichloromethane, and this mixture was ice-cooled. Then, to this mixture was added 3.025 g of chloromethyl-chlorosulfonate, and the reaction mixture was stirred for 0.5 hour at the same temperature and for 3 hours at room temperature. After the reaction, the organic layer was separated, washed with saturated saline solution and dried over magnesium sulfate. After removal of the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane: chloroform=3:1) to give 1.38 g (60%) of isovaleryloxy-methylchloride [Compound (2)].

Workup

  1. temperaturecooled
  2. customAfter the reaction
  3. customthe organic layer was separated
  4. washwashed with saturated saline solution
  5. dry with materialdried over magnesium sulfate
  6. customAfter removal of the solvent under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (hexane: chloroform=3:1)

Sources & evidence

ORD record
ord-6701e51660884ff3ad003b970062b79f
Source dataset
uspto-grants-1999_03
Patent number
US05886172

Reaction notes

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