Dimethoxymethane → 3-(Methoxymethoxy)benzaldehyde

HRID 1288108Notes

Reaction equation

HRID 1288108 reaction equation
[OH2:1].[C:2]1([CH3:12])[CH:7]=[CH:6][C:5](S(O)(=O)=O)=[CH:4][CH:3]=1.[CH3:13][O:14][CH2:15][O:16]C>C(Cl)Cl>[CH3:13][O:14][CH2:15][O:16][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[CH:12]=[O:1]

Participants

4

Reactant 2

HCID 8020DimethoxymethaneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 122735133-(Methoxymethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a preferred embodiment of the invention, m-hydroxybenzaldehyde and dimethoxymethane are dissolved in methylene chloride and p-toluenesulfonic acid monohydrate is added. The mixture is refluxed overnight using a Soxhlet extractor containing type 3A molecular sieves, and the product, m-methoxymethoxybenzaldehyde, is isolated and purified by standard procedures. For example, after the reaction mixture cools, triethylamine is added to neutralize the acid catalyst and the mixture is washed with dilute sodium hydroxide solution and water, dried over sodium sulfate and evaporated. The residue is purified by distillation.

Workup

  1. temperatureThe mixture is refluxed overnight

Sources & evidence

ORD record
ord-990c1a175afc4bae82e86b792fcf5b6c
Source dataset
uspto-grants-1976_10
Patent number
US03987105

Reaction notes

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