Benzene → m-(2,2-Dimethoxyethoxy)benzaldehyde

HRID 1680306Notes

Reaction equation

HRID 1680306 reaction equation
[OH-:1].[Na+].[CH3:3][O:4][CH:5]([O:8][CH3:9])[CH2:6]Br.[CH:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:16]([O:18]CCO)C>>[CH3:3][O:4][CH:5]([O:8][CH3:9])[CH2:6][O:1][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=[O:18])[CH:11]=1

Participants

5

Reactant 4

HCID 241BenzeneHCID 8076Glycol monoethyl etherHCID 14798Sodium HydroxideHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 20572041m-(2,2-Dimethoxyethoxy)benzaldehyde

Procedure

In 10 ml of 2-ethoxyethyl alcohol were dissolved 4.88 g of m-hydroxybenzaldehyde and 1.65 g of caustic soda. The resultant solution, after addition thereto of 7.4 g of bromoacetaldehyde dimethylacetal, was refluxed for 20 hours. The resultant reaction solution was cooled, mixed with benzene, washed once with water and then washed with a dilute alkali solution until the hydroxyaldehyde was completely removed. When the benzene solution was desiccated over anhydrous potassium carbonate and then distilled, there was obtained 3.6 g of m-formylphenoxyacetaldehyde dimethyl acetal (bp3 138° C.). By repeating this procedure faithfully by using o-hydroxybenzaldehyde, there were obtained o-formylphenoxyacetaldehyde dimethylacetal (bp5 147° C.) and γ-(p-formylphenoxy)-butylaldehyde dimethyl acetal (bp3 168° C.).

Workup

  1. customThe resultant reaction solution
  2. temperaturewas cooled
  3. washwashed once with water
  4. washwashed with a dilute alkali solution until the hydroxyaldehyde
  5. customwas completely removed
  6. distillationdistilled

Sources & evidence

ORD record
ord-6b09f090f0004b42915c182452103dfd
Source dataset
uspto-grants-1981_06
Patent number
US04272620

Reaction notes

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