Thionyl Chloride → 2-(Chloromethyl)-6-methoxynaphthalene

HRID 2419930Notes

Reaction equation

HRID 2419930 reaction equation
O[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH3:14])[CH:9]=2)[CH:4]=1.S(Cl)([Cl:17])=O>>[Cl:17][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH3:14])[CH:9]=2)[CH:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 10012701(6-methoxynaphthalen-2-yl)methanol

Product 1

HCID 133842572-(Chloromethyl)-6-methoxynaphthalene

Procedure

The 2-chloromethyl-6-methoxynaphthalene used as starting material is obtained from methyl 6-methoxy-2-naphthoate by reaction with sodium dihydro-bis-(2-methoxyethoxy)aluminate to give 2-hydroxymethyl-6-methoxynaphthalene, m.p. 118°-120° C. and reaction with thionyl chloride to give 2-chloromethyl-6-methoxynaphthalene, m.p. 63°-65° C. by the general procedure described in Example 4 for the preparation of 2-chloromethyl-6-chloronaphthalene.

Workup

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Sources & evidence

ORD record
ord-e22d33c3a9e1433fbd13d941ca0999c1
Source dataset
uspto-grants-1978_08
Patent number
US04107329

Reaction notes

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