Cyanide → 3-Phenoxybenzaldehyde

HRID 1413578Notes

Reaction equation

HRID 1413578 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:13]=[C:12]([CH:14]([OH:17])C#N)[CH:11]=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[C-]#N.[C-]#N.[Na+]>>[O:7]([C:8]1[CH:13]=[C:12]([CH:11]=[CH:10][CH:9]=1)[CH:14]=[O:17])[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 5975CyanideHCID 8929Sodium CyanideHCID 93218Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-

Product 1

HCID 382843-Phenoxybenzaldehyde

Procedure

As has been indicated above, m-phenoxybenzyl chloride, alone or in admixture with m-phenoxybenzal chloride, may be converted to m-phenoxybenzaldehyde by a Sommelet reaction, using hexamine (or ammonia and formaldehyde) and an aqueous organic acid. If the Sommelet reaction is carried out in the presence of other compounds such as unreacted m-phenoxytoluene, the crude m-phenoxybenzaldehyde is isolated by extraction with a suitable solvent such as diisopropyl ether and it may then be purified by preparing the corresponding bisulphite compound, washing it with solvent and subsequently regenerating the pure aldehyde by treatment with an acid or base. Alternatively, the bisulphite compound may be isolated and dried to obtain a pure material which can be converted directly to m-phenoxybenzaldehyde cyanohydrin by reaction with a cyanide such as sodium cyanide, thereby avoiding the additional stage of isolating the purified m-phenoxybenzaldehyde.

Workup

  1. custommay then be purified by preparing the corresponding bisulphite compound
  2. washwashing it with solvent
  3. customAlternatively, the bisulphite compound may be isolated
  4. customdried
  5. customto obtain a pure material which

Sources & evidence

ORD record
ord-80e474656b3345379bf9563f56b5f8fc
Source dataset
uspto-grants-1981_02
Patent number
US04250340

Reaction notes

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