Thionyl Chloride → Ethyl 2-(chlorocarbonyl)-2-methoxypropionate

HRID 893220Notes

Reaction equation

HRID 893220 reaction equation
[CH3:1][O:2][C:3]([CH3:12])([C:9]([O-])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].S(Cl)([Cl:15])=O>>[Cl:15][C:9]([C:3]([O:2][CH3:1])([CH3:12])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:10]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 86745933HCID 86745933, compound

Product 1

HCID 19096847Ethyl 2-(chlorocarbonyl)-2-methoxypropionateYield 100%

Procedure

Mon-ethyl methoxy(methyl)malonate (14.52 grams, 0.08 mole) was reacted with thionyl chloride (19.61 grams, 0.16 mole) at 50° C. for a 13-hour reaction period with an additional holding period of approximately 32 hours at room temperature. Vacuum evaporation of the excess thionyl chloride gave 15.2 grams (0.08 mole) of ethyl 2-(chlorocarbonyl)-2-methoxypropionate. NMR analysis of the product indicated the following:

Workup

  1. customreaction period with an additional holding period of approximately 32 hours at room temperature
  2. customVacuum evaporation of the excess thionyl chloride

Sources & evidence

ORD record
ord-e9cff9277721458b8b5cff4952132e3b
Source dataset
uspto-grants-1992_06
Patent number
US05123951

Reaction notes

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