Bis(2-chloroethyl) ether → 2,3-Dimethoxy-6-chlorotoluene

HRID 2121084Notes

Reaction equation

HRID 2121084 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[O:10][CH3:11].[Cl:12]CCOCCCl>C(O)(=O)C.O>[CH3:11][O:10][C:3]1[C:4]([O:8][CH3:9])=[CH:5][CH:6]=[C:7]([Cl:12])[C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 8115Bis(2-chloroethyl) etherHCID 782153-Methylveratrole

Product 1

HCID 234367502,3-Dimethoxy-6-chlorotolueneYield 67,980.102%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a mixture of 25 g (0.16 mmol) of 1-methyl-2,3-dimethoxybenzene in 25 mL of acetic acid, was slowly added 26.4 g (0.33 mmol) of 1-chloromethylmethylether. The resultant reaction mixture was reacted overnight at 30° C. and then diluted with cold water, resulting in the formation of a precipitate. This precipitate was purified by recrystallization from hot hexanes and then reduced to dryness under reduced pressure to provide 20.3 g of a white solid (m.p. 69-70° C.).

Workup

  1. customThe resultant reaction mixture
  2. customwas reacted overnight at 30° C.
  3. customresulting in the formation of a precipitate
  4. customThis precipitate was purified by recrystallization from hot hexanes

Sources & evidence

ORD record
ord-9fcf001c80c443c9b7fb9daf3e38e881
Source dataset
uspto-grants-2004_02
Patent number
US06693199B2

Reaction notes

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