Methyl chloroacetate → Methyl alpha-(3,5,6-trichloropyridyl)acetate

HRID 918048Notes

Reaction equation

HRID 918048 reaction equation
[Cl:1][C:2]1[C:3]([C:10]([O-])=O)=[N:4][C:5]([Cl:9])=[C:6]([Cl:8])[CH:7]=1.[Na+].ClC[C:16]([O:18][CH3:19])=[O:17]>C1(C)C=CC=CC=1.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:1][C:2]1[C:3]([CH2:10][C:16]([O:18][CH3:19])=[O:17])=[N:4][C:5]([Cl:9])=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 2

HCID 7295Methyl chloroacetateHCID 23699972Sodium 3,5,6-trichloropyridinate

Product 1

HCID 21522714Methyl alpha-(3,5,6-trichloropyridyl)acetateYield 90%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

Essentially equimolar amounts of sodium 3,5,6-trichloropyridinate and methyl α-chloroacetate in toluene were blended together in the presence of from 2 to 5 mole percent of benzyltriethylammonium chloride and the mixture refluxed at 105°C for 3 hours. The product, methyl α-(3,5,6-trichloropyridyl)acetate, was thus obtained in approximately 90 percent yield.

Sources & evidence

ORD record
ord-a5a9ef5a235a4867971ad1584a60e55c
Source dataset
uspto-grants-1976_07
Patent number
US03969360

Reaction notes

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