Chloromethyl Methyl Ether → 3-(Chloromethyl)-2-hydroxy-5-nitrobenzaldehyde

HRID 1109433Notes

Reaction equation

HRID 1109433 reaction equation
[N+:1]([C:4]1[CH:11]=[C:8]([CH:9]=[O:10])[C:7]([OH:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].CO[CH2:15][Cl:16].[Cl-].[Al+3].[Cl-].[Cl-]>O>[Cl:16][CH2:15][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:11]=[C:8]([CH:9]=[O:10])[C:7]=1[OH:12]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 668085-NitrosalicylaldehydeHCID 6451240Aluminum(III) Chloride

Product 1

HCID 993803-(Chloromethyl)-2-hydroxy-5-nitrobenzaldehydeYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 12.0 g of 5-nitrosalicylaldehyde and 100 ml of chloromethyl methyl ether was cooled on an ice-bath and 43.9 g of anhydrous aluminum chloride was added in small portions. The mixture was stirred at room temperature for 10 minutes and, then, refluxed for 22 hours. This reaction mixture was cooled on an ice-bath and 200 ml of water was added with vigorous stirring, whereupon white crystals separated out. These white crystals are collected, dissolved in hot hexane and filtered and the mother liquor was cooled to give 14.9 g of 3-chloromethyl-5-nitrosalicylaldehyde as colorless needles (Yield 72%).

Workup

  1. temperaturewas cooled on an ice-bath
  2. temperaturerefluxed for 22 hours
  3. temperatureThis reaction mixture was cooled on an ice-bath
  4. customseparated out
  5. customThese white crystals are collected
  6. dissolutiondissolved in hot hexane
  7. filtrationfiltered
  8. temperaturethe mother liquor was cooled

Sources & evidence

ORD record
ord-2a311c2454d546dc8212ea39fd7b2437
Source dataset
uspto-grants-1994_06
Patent number
US05320784

Reaction notes

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