Hydrochloric Acid → 3-Phenoxybenzaldehyde

HRID 971968Notes

Reaction equation

HRID 971968 reaction equation
Cl.[O:2]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#N)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH2:17]>CCOCC>[O:2]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=[O:17])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 34141613-Phenoxybenzonitrile

Product 1

HCID 382843-Phenoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Hydrogen chloride was introduced until saturation into a solution of 37.9 g of anhydrous stannous chloride (0.2 mole) in 200 ml of anhydrous ether. To the resulting solution, was added 19.5 g of 3-phenoxybenzonitrile (0.1 mole) and the mixture was stirred for 10 hours at room temperature. After addition of 200 ml of water and thorough stirring, the insoluble matter was removed by filtration. The filtrate was separated and the ether layer was further washed three times with 50 ml of water. After removal of the ether by distillation, the residue was distilled to obtain 8.5 g of crude 3-phenoxybenzaldehyde boiling at 100° to 115° C./0.45 mmHg which contained 71.4% of 3-phenoxybenzaldehyde.

Workup

  1. customthe insoluble matter was removed by filtration
  2. customThe filtrate was separated
  3. washthe ether layer was further washed three times with 50 ml of water
  4. customAfter removal of the ether
  5. distillationby distillation
  6. distillationthe residue was distilled

Sources & evidence

ORD record
ord-61af36005c8d4be0888ee0b379858aff
Source dataset
uspto-grants-1979_07
Patent number
US04162269

Reaction notes

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