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

HRID 1656123Notes

Reaction equation

HRID 1656123 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-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

While cooling a mixture of 12.0 g of 5-nitrosalicylaldehyde and 100 ml of chloromethyl methyl ether in an ice bath, 43.9 g of anhydrous aluminum chloride was added in small portions to the mixture, followed by stirring at room temperature for 10 minutes and thereafter by refluxing with heating for 22 hours. The reaction mixture was then cooled in an ice bath, and 200 ml of water was added to the mixture with full stirring, whereby white crystals were separated out. The white crystals were collected and dissolved in hot hexane, and the solution was filtered. The mother liquor was thereafter cooled, giving 14.9 g of 3-chloromethyl-5-nitrosalicylaldehyde in the form of white needlelike crystals (yield 72%).

Workup

  1. temperatureWhile cooling
  2. temperatureby refluxing
  3. temperaturewith heating for 22 hours
  4. temperatureThe reaction mixture was then cooled in an ice bath
  5. customwere separated out
  6. customThe white crystals were collected
  7. dissolutiondissolved in hot hexane
  8. filtrationthe solution was filtered
  9. temperatureThe mother liquor was thereafter cooled

Sources & evidence

ORD record
ord-906540cfcf1143d7bfb31aa701b01a45
Source dataset
uspto-grants-1993_10
Patent number
US05252742

Reaction notes

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