Thionyl Chloride → Methyl (2-chloromethyl-5-methylphenoxy)acetate

HRID 2225414Notes

Reaction equation

HRID 2225414 reaction equation
O[CH2:2][C:3]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:4]=1[O:5][CH2:6][C:7]([O:9][CH3:10])=[O:8].S(Cl)([Cl:18])=O>N1C=CC=CC=1.C(Cl)Cl>[Cl:18][CH2:2][C:3]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:4]=1[O:5][CH2:6][C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 54364037Methyl (2-hydroxymethyl-5-methylphenoxy)acetate

Product 1

HCID 53932989Methyl (2-chloromethyl-5-methylphenoxy)acetateYield 55.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

By the method of Example 1, Step H, 9.21 g (0.044 mole) of methyl (2-hydroxymethyl-5-methylphenoxy)acetate was reacted with 7.40 g (0.062 mole) of thionyl chloride and 5 drops of pyridine in 50 mL of methylene chloride, yielding 5.57 g of methyl (2-chloromethyl-5-methylphenoxy)acetate as an orange liquid.

Sources & evidence

ORD record
ord-8089a57734ec44e28a5035f0c0449faf
Source dataset
uspto-grants-1994_09
Patent number
US05344812

Reaction notes

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