Thionyl Chloride → Methyl 2-(3-chloromethylphenoxy)propionate

HRID 257392Notes

Reaction equation

HRID 257392 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[O:6][CH:7]([CH3:12])[C:8]([O:10][CH3:11])=[O:9].S(Cl)([Cl:18])=O>N1C=CC=CC=1.C(Cl)Cl>[Cl:18][CH2:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[O:6][CH:7]([CH3:12])[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 18759680Methyl 2-(3-hydroxymethylphenoxy)propionate

Product 1

HCID 18981053Methyl 2-(3-chloromethylphenoxy)propionateYield 88.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

By the method of Example 1, Step J, 1.98 g (0.0095 mole) of methyl 2-(3-hydroxymethylphenoxy)propionate and 1.24 g (0.0105 mole) of thionyl chloride were reacted in the presence of five drops of pyridine in 40 mL of methylene chloride, yielding 1.93 g of methyl 2-(3-chloromethylphenoxy)propionate as a yellow liquid. The NMR and IR spectra were consistent With the proposed structure.

Sources & evidence

ORD record
ord-db3e6a09383f412a9ac05f4827ce892e
Source dataset
uspto-grants-1993_11
Patent number
US05262390

Reaction notes

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