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

HRID 441105Notes

Reaction equation

HRID 441105 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].[Cl-].[Al+3].[Cl-].[Cl-].CO[CH2:19][Cl:20]>>[Cl:20][CH2:19][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

4

Reactant 3

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

Product 1

HCID 993803-(Chloromethyl)-2-hydroxy-5-nitrobenzaldehyde

Procedure

5-Nitrosalicylaldehyde (2.42 g, 14.5 mmols) was suspended in 20 ml of chloromethyl methyl ether, and aluminum chloride (7.97 g, 60.0 mmols) was added while cooling in an ice bath. After stirring at room temperature for 10 minutes, the mixture was heated at 60° C. for one hour. Then, the reaction solution was poured into 100 ml of ice water while cooling in an ice bath and the resulting yellow precipitate was filtered. The resulting precipitate was recrystallized from 330 ml of hexane to give 3-chloromethyl-5-nitrosalicylaldehyde (2.49 g, 11.6 mmols) as a yellow needle-like crystal (yield 80%).

Workup

  1. temperaturewhile cooling in an ice bath
  2. temperaturethe mixture was heated at 60° C. for one hour
  3. temperaturewhile cooling in an ice bath
  4. filtrationthe resulting yellow precipitate was filtered
  5. customThe resulting precipitate was recrystallized from 330 ml of hexane

Sources & evidence

ORD record
ord-ce18bc7c8f664e5ba842a6df5657b2fa
Source dataset
uspto-grants-1996_05
Patent number
US05521269

Reaction notes

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