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

HRID 2254674Notes

Reaction equation

HRID 2254674 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[N+:5]([C:8]1[CH:15]=[C:12]([CH:13]=[O:14])[C:11]([OH:16])=[CH:10][CH:9]=1)([O-:7])=[O:6].CO[CH2:19][Cl:20]>O>[Cl:20][CH2:19][C:10]1[CH:9]=[C:8]([N+:5]([O-:7])=[O:6])[CH:15]=[C:12]([CH:13]=[O:14])[C:11]=1[OH:16]

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 43.9 g (0.33 mole) quantity of anhydrous aluminum chloride was added in small portions to a mixture of 12.0 g (71.8 mmoles) of 5-nitrosalicylaldehyde and 100 ml of chloromethyl methyl ether with cooling in an ice bath. The resulting mixture was stirred at room temperature for 10 minutes and refluxed with heating for 22 hours. Thereafter, the reaction mixture was cooled in an ice bath, followed by addition of 200 ml of water with thorough stirring, whereby white crystals were precipitated. The white crystals were collected, dissolved in hot hexane and filtered. The mother liquor was cooled, giving 14.9 g (yield: 72%) of 3-chloromethyl-5-nitrosalicylaldehyde as colorless needle crystals.

Workup

  1. temperaturewith cooling in an ice bath
  2. temperaturerefluxed
  3. temperaturewith heating for 22 hours
  4. temperatureThereafter, the reaction mixture was cooled in an ice bath
  5. customwere precipitated
  6. customThe white crystals were collected
  7. dissolutiondissolved in hot hexane
  8. filtrationfiltered
  9. temperatureThe mother liquor was cooled

Sources & evidence

ORD record
ord-3a883df4f37c4043a1dcea8c228f388e
Source dataset
uspto-grants-1993_08
Patent number
US05236958

Reaction notes

Loading…