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

HRID 2255644Notes

Reaction equation

HRID 2255644 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 portionwise to said mixture, and the resultant mixture was stirred at room temperature for 10 minutes and then heated under reflux for 22 hours. Then, the reaction mixture was cooled on an ice bath and 200 ml of water was added thereto with vigorous stirring, whereupon white crystals precipitated out. These white crystals were taken out and dissolved in hot hexane, and the solution was 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. temperatureheated
  3. temperatureunder reflux for 22 hours
  4. temperatureThen, the reaction mixture was cooled on an ice bath
  5. customwith vigorous stirring, whereupon white crystals precipitated out
  6. dissolutiondissolved in hot hexane
  7. filtrationthe solution was filtered
  8. temperaturethe mother liquor was cooled

Sources & evidence

ORD record
ord-502794f0e6c14497bd45f5f718fcd8fb
Source dataset
uspto-grants-1993_08
Patent number
US05241027

Reaction notes

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