Methyl iodide → 6-Methoxy-2,4-bis(trichloromethyl)-2H,4H-1,3-benzodioxine

HRID 224411Notes

Reaction equation

HRID 224411 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH:11]([C:13]([Cl:16])([Cl:15])[Cl:14])[O:10][CH:9]([C:17]([Cl:20])([Cl:19])[Cl:18])[C:8]=2[CH:21]=1.[CH3:22]I>C(O)C>[CH3:22][O:3][C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH:11]([C:13]([Cl:14])([Cl:15])[Cl:16])[O:10][CH:9]([C:17]([Cl:20])([Cl:19])[Cl:18])[C:8]=2[CH:21]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 233329442,4-Bis(trichloromethyl)-2H,4H-1,3-benzodioxin-6-ol

Product 1

HCID 233329516-Methoxy-2,4-bis(trichloromethyl)-2H,4H-1,3-benzodioxine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of sodium hydroxide (0.52 g.) in ethanol (50 ml.) was added dropwise to a stirred solution of 6-hydroxy-2,4-bis(trichloromethyl)benzo[1,3]dioxin (5 g.) in ethanol (100 ml.) and the resulting solution was stirred for 15 minutes. Methyl iodide (1.7 ml.) was then added, the reaction mixture was warmed on a steam bath for 1 hour, and evaporated to dryness under reduced pressure, and the oily residue was triturated with diethyl ether and filtered to remove sodium iodide. The filtrate was chromatographed on silica (Kieselgel 60; 200 g.) and the product was crystallised from ethanol to give 6-methoxy-2,4-bis(trichloromethyl)benzo[1,3]dioxin, m.p. 105°-107° C.

Workup

  1. temperaturethe reaction mixture was warmed on a steam bath for 1 hour
  2. customevaporated to dryness under reduced pressure
  3. customthe oily residue was triturated with diethyl ether
  4. filtrationfiltered
  5. customto remove sodium iodide
  6. customThe filtrate was chromatographed on silica (Kieselgel 60; 200 g.)
  7. customthe product was crystallised from ethanol

Sources & evidence

ORD record
ord-b2a67344d84446508a6a96f2028a4897
Source dataset
uspto-grants-1980_11
Patent number
US04232032

Reaction notes

Loading…