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

HRID 2255643Notes

Reaction equation

HRID 2255643 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]>>[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

4

Reactant 3

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

Product 1

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

Procedure

Aluminum chloride (80 g) was added to an ice bath-cooled mixture of 20.0 g of 5-nitrosalicylaldehyde and 200 ml of chloromethyl methyl ether, and the reaction was carried out at room temperature for 1 hour and then at 63° C. for 17 hours. The reaction mixture was cooled on an ice bath, and then 300 ml of ice water was added, and the resultant white precipitate was collected by filtration and recrystallized from hexane to give 18.6 g of 3-chloromethyl-5-nitrosalicylaldehyde (yield 72%).

Workup

  1. temperaturebath-cooled
  2. waitat 63° C. for 17 hours
  3. temperatureThe reaction mixture was cooled on an ice bath
  4. filtrationthe resultant white precipitate was collected by filtration
  5. customrecrystallized from hexane

Sources & evidence

ORD record
ord-aebbeec93a134862bbdbba6ffb69b468
Source dataset
uspto-grants-1993_08
Patent number
US05241027

Reaction notes

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