Sulfuryl chloride → Methyl 2-chloro-3-oxopentanoate

HRID 582893Notes

Reaction equation

HRID 582893 reaction equation
[O:1]=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5].S(Cl)([Cl:13])(=O)=O>C1(C)C=CC=CC=1>[Cl:13][CH:3]([C:2](=[O:1])[CH2:8][CH3:9])[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 121699Methyl 3-oxovalerate

Product 1

HCID 545096Methyl 2-chloro-3-oxopentanoateYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 104 g (0.8 mol) of methyl 3-oxopentanoate (available from Wacker Chemical) in 500 ml of toluene was cooled to 0 to 5° C., and 108 g (0.8 mol) of sulfuryl chloride was added thereto dropwise, followed by stirring at room temperature overnight. Toluene was removed by evaporation to give 131.6 g (0.8 mol; yield: 100%) of the title compound.

Workup

  1. customToluene was removed by evaporation

Sources & evidence

ORD record
ord-ce6cc85c8fe24531bb5ad656f02fac70
Source dataset
uspto-grants-1999_07
Patent number
US05925792

Reaction notes

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