Thionyl Chloride → Methyl 2-(2-chloromethyl-5-chlorophenoxy)propionate

HRID 1488395Notes

Reaction equation

HRID 1488395 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:15]O)=[C:6]([CH:14]=1)[O:7][CH:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10].S(Cl)([Cl:19])=O>C(Cl)Cl>[Cl:19][CH2:15][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:14][C:6]=1[O:7][CH:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 53695259Methyl 2-(5-chloro-2-hydroxymethylphenoxy)propionate

Product 1

HCID 53768369Methyl 2-(2-chloromethyl-5-chlorophenoxy)propionateYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By the method of Example 1, Step H, 1.0 g (0.0038 mole) of methyl 2-(5-chloro-2-hydroxymethylphenoxy)propionate and 0.5 g (0.0042 mole) of thionyl chloride were reacted in 20 mL of methylene chloride. After purification, 0.88 g of methyl 2-(2-chloromethyl-5-chlorophenoxy)propionate was isolated as a yellow liquid. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customAfter purification

Sources & evidence

ORD record
ord-801eb85a46644798b0ac41926da290d0
Source dataset
uspto-grants-1997_10
Patent number
US05674810

Reaction notes

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