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Carbon Tetrachloride → Dimethyl alpha-chloro-alpha-methylmalonate

HRID 654604
Notes
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Reaction equation

HRID 654604 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.C(=O)([O-])[O-].[K+].[K+]>[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11430Potassium CarbonateHCID 69104Dimethyl methylmalonate

Product 1

HCID 10943067Dimethyl alpha-chloro-alpha-methylmalonateYield 99.7%

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), 0.27 g potassium carbonate (2 mmol), and 63 mg tetra-n-butylammonium fluoride (0.2 mmol) was mixed by a magnetic stirrer at 24° C. for 5 h. The product mixture was filtered, and gas chromatographic analysis of the filtrate showed the presence of 1.8 g of dimethyl α-chloro-α-methylmalonate (99% yield).

Workup

  1. additionwas mixed by a magnetic stirrer at 24° C. for 5 h
  2. filtrationThe product mixture was filtered

Sources & evidence

ORD record
ord-eed56e225b3b44659da8d4af25da8327
Source dataset
uspto-grants-1992_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05132475

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes