Pyridine → HCID 14093553, compound

HRID 1904438Notes

Reaction equation

HRID 1904438 reaction equation
[CH3:1][O:2][CH2:3][C:4]([CH3:11])([CH2:9]O)[C:5]([O:7][CH3:8])=[O:6].S(Cl)([Cl:14])=O.N1C=CC=CC=1>>[CH3:1][O:2][CH2:3][C:4]([CH3:11])([CH2:9][Cl:14])[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 14093551HCID 14093551, compound

Product 1

HCID 14093553HCID 14093553, compoundYield 91%

Conditions

Temperature
60 °C

Procedure

The methyl 2-methoxymethyl-2-methyl-3-hydroxypropionate was added at from 15° to 20° C. to 438 g (3.68 mol) of thionyl chloride, the temperature was then raised to 60° C. and the mixture was stirred until the evolution of gas had ended. Excess thionyl chloride was distilled off, 0.2 g (0.0025 mol) of pyridine was added to the residue, and the temperature was raised to 135° C. After the evolution of SO2 had ended, distillation gave 317.0 g (1.76 mol) of methyl 2-methoxymethyl-2-methyl-3chloropropionate of boiling point 94° C. 35 mbar, corresponding to a 91% yield, based on methyl 2-methoxymethyl-2-methyl-3-hydroxypropionate.

Workup

  1. distillationExcess thionyl chloride was distilled off
  2. temperaturethe temperature was raised to 135° C
  3. distillationdistillation

Sources & evidence

ORD record
ord-39ca00056cb94ebaa3e22d119db013fe
Source dataset
uspto-grants-1989_06
Patent number
US04837357

Reaction notes

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