Chloromethyl Methyl Ether → HCID 21432118, compound

HRID 2398932Notes

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:13][CH2:14]OC>>[Cl:13][CH2:14][C:5]1[CH:6]=[C:7]([OH:12])[C:8](=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])[CH:9]=[O:10]

Participants

Reactant 2

HCID 7864Chloromethyl Methyl Ether

HCID 668085-Nitrosalicylaldehyde

Product 1

HCID 21432118HCID 21432118, compound

Procedure

5-nitrosalicylaldehyde was obtained upon reaction of salicylaldehyde with nitric acid according to the method described by G. Miller in Chem. Ber., 20, 1928 (1888). This 5-nitrosalicylaldehyde was made to react with chloromethyl-methyl ether according to D. Taylor and B. Davis, J. Org. Chem., 28, 1713 (1963) to form 4-chloromethyl-5-nitro-salicylaldehyde, which was converted into the 4-hydroxymethyl derivative by refluxing the chloromethyl derivative for 3 hours in water. The 4-hydroxymethyl-5-nitro-salicylaldehyde had a melting point of 135°C.

Sources & evidence

ORD record: ord-0cfd7571ac08407da71d76b8d54b028a
Source dataset: uspto-grants-1977_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04026869

Reaction notes

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