Pyridine → 3-Phenoxybenzaldehyde

HRID 1731563Notes

Reaction equation

HRID 1731563 reaction equation
N1C=CC=CC=1.[O:7]([C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17][OH:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(Cl)Cl.[O-2].[O-2].[O-2].[Cr+6]>[O:7]([C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=[O:18])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 1049PyridineHCID 262953-Phenoxybenzyl alcohol

Product 1

HCID 382843-Phenoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Chromium trioxide (3.00 g.) was added to a stirred solution of pyridine (4.75 g.) in dry methylene chloride (75 ml.), and stirring was continued for a further 15 minutes. 3-Phenoxybenzyl alcohol (1 g.) in methylene chloride (5 ml.) was added, the mixture stirred for a further 15 minutes, decanted and the residue washed with diethyl ether (100 ml.). The filtrate was washed with 5% sodium hydroxide solution (3×50 ml), 2.5 NHCl (50 ml.) and 5% sodium carbonate solution (50 ml.) and dried over Na2SO4 to give 3-phenoxy-benzaldehyde. Alternatively the alcohol can be oxidized using Jones' reagent, a similar yield of aldehyde being obtained.

Workup

  1. stirringthe mixture stirred for a further 15 minutes
  2. customdecanted
  3. washthe residue washed with diethyl ether (100 ml.)
  4. washThe filtrate was washed with 5% sodium hydroxide solution (3×50 ml), 2.5 NHCl (50 ml.) and 5% sodium carbonate solution (50 ml.)
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-77086e00b24c4de2abae4b6ed1587507
Source dataset
uspto-grants-1986_11
Patent number
US04622337

Reaction notes

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