Hydrochloric Acid → 3-Phenoxybenzaldehyde

HRID 224270Notes

Reaction equation

HRID 224270 reaction equation
Cl.[OH2:2].[O:3]([C:10]1[CH:11]=[C:12]([CH:19]=[CH:20][CH:21]=1)[CH:13]=NCC(C)C)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C1(C)C=CC=CC=1>[O:3]([C:10]1[CH:11]=[C:12]([CH:19]=[CH:20][CH:21]=1)[CH:13]=[O:2])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 233324743-Phenoxybenzylidene-isobutylamine

Product 1

HCID 382843-PhenoxybenzaldehydeYield 94.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20 g of 37% hydrochloric acid (about 0.2 mol) and 20 ml of water are added, with stirring, to a solution of 40 g (0.158 mol) of 3-phenoxybenzylidene-isobutylamine in 40 ml of toluene, and the whole is refluxed for 15 minutes. The organic phase is separated; it is then washed neutral with 10% sodium hydrogen carbonate solution, and the toluene is removed by rotation in a slight water-jet vacuum. Distillation of the residue yields 29.7 g (0.15 mol) of 3-phenoxybenzaldehyde, corresponding to a yield of 94.9% of theory; b.p. 94° C./6 Pa; nD20 =1.5976.

Workup

  1. temperaturethe whole is refluxed for 15 minutes
  2. customThe organic phase is separated
  3. washit is then washed neutral with 10% sodium hydrogen carbonate solution
  4. customthe toluene is removed by rotation in a slight water-jet vacuum
  5. distillationDistillation of the residue

Sources & evidence

ORD record
ord-2e0fa9313051494aba91e78764bf09e3
Source dataset
uspto-grants-1980_11
Patent number
US04231962

Reaction notes

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