Acetic Acid → Phenoxyacetaldehyde

HRID 1942441Notes

Reaction equation

HRID 1942441 reaction equation
C([O:3][CH:4](OCC)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.C(O)(=O)C.Cl>C(O)C>[O:6]([CH2:5][CH:4]=[O:3])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 96328(2,2-Diethoxyethoxy)benzene

Product 1

HCID 75033Phenoxyacetaldehyde

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.84 g (4 mmol) of 69A, 5 mL of acetic acid, 2.5 mL of 1N aqueous hydrochloric acid and 20 mL of ethanol were mixed and heated under reflux under an argon atmosphere for 3 hours. Ethanol was evaporated. Then the resulting residue was dispersed in dichloromethane and extracted with saturated sodium bicarbonate solution. The organic phase was dried with sodium sulfate and the solvent evaporated in vacuum. The crude product was obtained in almost quantitative yield.

Workup

  1. temperatureheated
  2. temperatureunder reflux under an argon atmosphere for 3 hours
  3. customEthanol was evaporated
  4. additionThen the resulting residue was dispersed in dichloromethane
  5. extractionextracted with saturated sodium bicarbonate solution
  6. dry with materialThe organic phase was dried with sodium sulfate
  7. customthe solvent evaporated in vacuum

Sources & evidence

ORD record
ord-2ec187ccb9594cdb8a00a7050c53f9f6
Source dataset
uspto-grants-2013_03
Patent number
US08389555B2

Reaction notes

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