2,4,6-Trimethylpyridine → 2-(chloromethyl)-1,4-dimethoxybenzene

HRID 66636Notes

Reaction equation

HRID 66636 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:8]=1[CH2:9]O.N1C(C)=CC(C)=CC=1C>C(Cl)Cl>[CH3:5][O:6][C:7]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:8]=1[CH2:9][Cl:3]

Participants

5

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 24386Thionyl ChlorideHCID 1184952,5-Dimethoxybenzyl alcohol

Product 1

HCID 2911942-(chloromethyl)-1,4-dimethoxybenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (108 g) is slowly added during 1 hour to a stirred mixture of 2,5-dimethoxybenzyl alcohol (150 g), 2,4,6-collidine (108 g), and methylene chloride (750 ml) at room temperature. The reaction is slightly exothermic. After stirring for another 30 minutes, the mixture is washed with hydrochloric acid (2 N) and water and then dried (MgSO4). Evaporation gives a residue of 2,5-dimethoxybenzyl chloride which crystallizes (127 g).

Workup

  1. washthe mixture is washed with hydrochloric acid (2 N) and water
  2. dry with materialdried (MgSO4)
  3. customEvaporation

Sources & evidence

ORD record
ord-d43a9d1e222343dcb7312f5c3869d34c
Source dataset
uspto-grants-1982_08
Patent number
US04342780

Reaction notes

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