Toluene → 2-(Chloromethyl)-4-(3-methoxypropoxy)-3-methylpyridine

HRID 556015Notes

Reaction equation

HRID 556015 reaction equation
O[CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:6]=[CH:5][N:4]=1.C1(C)C=CC=CC=1.S(Cl)([Cl:25])=O>C(O)C>[Cl:25][CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 104657494-(3-Methoxypropoxy)-3-methyl-2-pyridinemethanol

Product 1

HCID 110316672-(Chloromethyl)-4-(3-methoxypropoxy)-3-methylpyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixed solution of 2-hydroxymethyl-4-(3-methoxypropoxy)-3-methylpyridine (12.02 g (56.9 mmol)) and toluene (96.0 ml) was added dropwise thionyl chloride (8.11 g (68.2 mmol)), so that the internal temperature did not exceed 25° C., which was stirred for about 90 minutes at room temperature. Ethanol (24.0 ml) was added to this mixed solution to obtain a 2-chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine solution.

Workup

  1. customdid not exceed 25° C.

Sources & evidence

ORD record
ord-12161e8f4c2d45a4a2d1aa4c111bb6ae
Source dataset
uspto-grants-2011_11
Patent number
US08053580B2

Reaction notes

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