Sulfuryl chloride → Decanoic acid, 3-oxo-, methyl ester

HRID 582889Notes

Reaction equation

HRID 582889 reaction equation
[O:1]=[C:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:3][C:4]([O:6][CH3:7])=[O:5].S(Cl)([Cl:18])(=O)=O>C1(C)C=CC=CC=1>[O:1]=[C:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[Cl:18][CH:3]([C:2](=[O:1])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 24648Sulfuryl chlorideHCID 89669Decanoic acid, 3-oxo-, methyl ester

Product 2

HCID 89669Decanoic acid, 3-oxo-, methyl esterHCID 54424532Methyl 2-chloro-3-oxodecanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
2.5 °C

Procedure

In 500 ml of toluene was dissolved 160 g (0.8 mol) of the resulting methyl 3-oxodecanoate, the solution 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 187.8 g (0.8 mol; yield: 100% from methyl 3-oxodecanoate) of the title compound.

Workup

  1. customToluene was removed by evaporation

Sources & evidence

ORD record
ord-7e39e4aa2d094d64af5bcc76a6c1c8f7
Source dataset
uspto-grants-1999_07
Patent number
US05925792

Reaction notes

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