Carbon Tetrachloride → Dimethyl alpha-chloro-alpha-methylmalonate

HRID 654603

Reaction equation

HRID 654603 reaction equation
[CH3:1][CH:2]([C:7]([O:9][CH3:10])=[O:8])[C:3]([O:5][CH3:6])=[O:4].[Cl:11]C(Cl)(Cl)Cl>[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:11][C:2]([CH3:1])([C:7]([O:9][CH3:10])=[O:8])[C:3]([O:5][CH3:6])=[O:4]

Participants

4

Reactant 2

HCID 5943Carbon TetrachlorideHCID 69104Dimethyl methylmalonate

Product 1

HCID 10943067Dimethyl alpha-chloro-alpha-methylmalonateYield 63.1%

Reagents, catalysts & solvents 1

HCID 2724141Tetrabutylammonium FluorideCatalyst

Procedure

In a 10 mL round-bottom flask, a mixture of 1.46 g dimethyl methylmalonate (10 mmol), 1.69 g tetrachloromethane (11 mmol), and 63 mg tetra-n-butylammonium fluoride (0.2 mmol) was mixed by a magnetic stirrer for 15 min at 24° C. Gas chromatographic analysis of the product mixture showed that the solution contained 1.14 g of dimethyl α-chloro-α-methylmalonate (63% yield).

Workup

  1. additionwas mixed by a magnetic stirrer for 15 min at 24° C

Sources & evidence

ORD record
ord-b04e98ad4b4442ffa79ccdf0dd51c413
Source dataset
uspto-grants-1992_07
Patent number
US05132475

Linked notes

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