Hydrochloric Acid → 4-Phenoxyphenoxyacetaldehyde

HRID 35277Notes

Reaction equation

HRID 35277 reaction equation
Cl.C([O:4][CH:5](OCC)[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)C>O1CCCC1>[O:14]([C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:6][CH:5]=[O:4])=[CH:9][CH:10]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 137717034-Phenoxyphenoxyacetaldehyde diethyl acetal

Product 1

HCID 194241144-Phenoxyphenoxyacetaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

280 ml of 1N HCl are added to a solution of 170 g of the acetal obtained in step (a) in 2000 ml of tetrahydrofuran, and the batch is stirred, under nitrogen, for 21 hours at 45° C. Subsequently, the tetrahydrofuran is distilled off in vacuo, the residue is taken up in diethyl ether and the resultant solution is washed repeatedly with saturated sodium bicarbonate solution and finally with water. The ethereal phase is dried over sodium sulfate and the solvent is distilled off entirely. The crude aldehyde is purified by chromatography over silica gel (eluant: a 1:1 mixture of diethyl ether and hexane), affording pure 4-phenoxyphenoxyacetaldehyde with a melting point of 79°-81° C.

Workup

  1. distillationSubsequently, the tetrahydrofuran is distilled off in vacuo
  2. washthe resultant solution is washed repeatedly with saturated sodium bicarbonate solution and finally with water
  3. dry with materialThe ethereal phase is dried over sodium sulfate
  4. distillationthe solvent is distilled off entirely
  5. customThe crude aldehyde is purified by chromatography over silica gel (eluant
  6. additiona 1:1 mixture of diethyl ether and hexane),

Sources & evidence

ORD record
ord-35200646ecd143279e0a6b21d531a9de
Source dataset
uspto-grants-1988_08
Patent number
US04766152

Reaction notes

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