Chloromethyl Methyl Ether → N-methoxymethyl-N-methylpyrrolidinium chloride

HRID 383177Notes

Reaction equation

HRID 383177 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:7][O:8][CH2:9][Cl:10]>C1(C)C=CC=CC=1>[Cl-:10].[CH3:1][N+:2]1([CH2:7][O:8][CH3:9])[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Conditions

Temperature
5 °C

Procedure

A 30.0 g quantity of N-methylpyrrolidine (reagent, product of Tokyo Kasei Co., Ltd.) was dissolved in 120 g of toluene, followed by replacement with nitrogen. Chloromethyl methyl ether (31.2 g, reagent, product of Tokyo Kasei Co., Ltd.) was added dropwise to the solution at 5° C. over a period of 1 hour. The mixture was stirred at 5° C. for 1 hour, then gradually heated to a higher temperature, and stirred at room temperature for 10 hours to complete the reaction. The reaction mixture was filtered, and the resulting solid product was washed with 150 g of toluene and 150 g of acetone. The washed product was dried in a vacuum to obtain 53.7 g of the desired product (white solid).

Workup

  1. temperaturegradually heated to a higher temperature
  2. stirringstirred at room temperature for 10 hours
  3. customthe reaction
  4. filtrationThe reaction mixture was filtered
  5. washthe resulting solid product was washed with 150 g of toluene and 150 g of acetone
  6. customThe washed product was dried in a vacuum

Sources & evidence

ORD record
ord-2297c9ba132c47f2a98b1e2367a9b2a2
Source dataset
uspto-grants-2013_02
Patent number
US08366956B2

Reaction notes

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