Pyridine → HCID 14093552, compound

HRID 1904437Notes

Reaction equation

HRID 1904437 reaction equation
[CH3:1][C:2]([CH2:9][CH3:10])([CH2:7]O)[C:3]([O:5][CH3:6])=[O:4].S(Cl)([Cl:13])=O.N1C=CC=CC=1>>[CH3:1][C:2]([CH2:9][CH3:10])([CH2:7][Cl:13])[C:3]([O:5][CH3:6])=[O:4]

Participants

4

Reactant 3

HCID 1049PyridineHCID 24386Thionyl Chloride2×HCID 14093550116623-21-3

Product 1

HCID 14093552HCID 14093552, compoundYield 93.2%

Conditions

Temperature
50 °C

Procedure

The methyl 2-methyl-2-ethyl-3-hydroxypropionate was added at below 20° C. to 178.6 g (1.5 mol) of thionyl chloride, and the mixture was stirred at 50° C. for a further 30 min. Excess thionyl chloride was then distilled off at 100 mbar, 0.5 g (0.006 mol) of pyridine was added to the residue, and the mixture was heated at from 130° to 135° C. for 45 min. Fractional distillation gave 114.4 g of methyl 2-methyl-2-ethyl-3-chloropropionate having a boiling point of 101°-104° C./8 mbar, corresponding to a 93.2% yield, based on methyl 2-methyl-2-ethyl-3-hydroxypropionate. The overall yield was 69.5%, based on 2-methyl-2-ethyl-3-hydroxypropanal.

Workup

  1. additionwas added to the residue
  2. temperaturethe mixture was heated at from 130° to 135° C. for 45 min
  3. distillationFractional distillation

Sources & evidence

ORD record
ord-0d0adced1e0747a5a9e29297954ffede
Source dataset
uspto-grants-1989_06
Patent number
US04837357

Reaction notes

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