Methyl chloroacetate → Acetic acid, 2-[(3,5,6-trichloro-2-pyridinyl)oxy]-, methyl ester

HRID 235987

Reaction equation

HRID 235987 reaction equation
[C:1](=O)([O:4][C:5]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[C:7]([Cl:13])[N:6]=1)OC.ClC[C:17]([O:19][CH3:20])=[O:18]>>[Cl:11][C:10]1[C:5]([O:4][CH2:1][C:17]([O:19][CH3:20])=[O:18])=[N:6][C:7]([Cl:13])=[C:8]([Cl:12])[CH:9]=1

Participants

3

Reactant 2

HCID 7295Methyl chloroacetateHCID 20218094Methyl 3,5,6-trichloro-2-pyridyl carbonate

Product 1

HCID 94596Acetic acid, 2-[(3,5,6-trichloro-2-pyridinyl)oxy]-, methyl ester

Procedure

Mixtures of 2.56 g (0.01 g mole) of methyl 3,5,6-trichloro-2-pyridyl carbonate, 0.01 to 0.1 g mole of methyl chloroacetate, and initiator as noted were heated at 100° C. until gas evolution had stopped. Unreacted methyl chloroacetate was then removed from the reaction mixture using a rotary evaporator. The crude product remaining was analyzed by gas chromatography. In each case, a good yield (about 2.8 g of crude product) of the expected 3,5,6-trichloro-2-pyridoxyacetic acid, methyl ester (III) was found with only small amounts of by-products IV, V, and VI as shown schematically below. ##STR2## The reaction conditions and results are listed in detail in Table II.

Workup

  1. customUnreacted methyl chloroacetate was then removed from the reaction mixture
  2. customa rotary evaporator

Sources & evidence

ORD record
ord-e7e1a05f5f7b4f89996c0768a813978b
Source dataset
uspto-grants-1987_02
Patent number
US04642349

Linked notes

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