4-(2-Chlorobenzyloxy)-3,5-dichlorophenoxyacetaldehyde diethyl acetal → 4-(2-Chlorobenzyloxy)-3,5-dichlorophenoxyacetaldehyde

HRID 363101Notes

Reaction equation

HRID 363101 reaction equation
C([O:3][CH:4](OCC)[CH2:5][O:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])=[C:9]([Cl:23])[CH:8]=1)C>C(O)(=O)C.Cl>[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:15][O:14][C:10]1[C:11]([Cl:13])=[CH:12][C:7]([O:6][CH2:5][CH:4]=[O:3])=[CH:8][C:9]=1[Cl:23]

Participants

4

Reactant 1

HCID 540752324-(2-Chlorobenzyloxy)-3,5-dichlorophenoxyacetaldehyde diethyl acetal

Product 1

HCID 540424034-(2-Chlorobenzyloxy)-3,5-dichlorophenoxyacetaldehydeYield 100%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

Then, 0.85 g of 4-(2-chlorobenzyloxy)-3,5-dichlorophenoxyacetaldehyde diethyl acetal was dissolved in 10 ml of acetic acid, to which 1 ml of concentrated hydrochloric acid was added dropwise, while stirring under ice cooling. After stirring under ice cooling for 2 hours, the reaction mixture was poured into ice water, and extracted twice with diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, followed by removal of the solvent by distillation under reduced pressure, which afforded 0.70 g of 4-(2-chlorobenzyloxy)-3,5-dichlorophenoxyacetaldehyde in crude form.

Workup

  1. additionwas added dropwise
  2. stirringAfter stirring under ice cooling for 2 hours
  3. extractionextracted twice with diethyl ether
  4. washThe combined ether layer was washed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customfollowed by removal of the solvent by distillation under reduced pressure, which

Sources & evidence

ORD record
ord-88c5b423bdda40c1910eda184048c88a
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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