4-Hydroxybenzaldehyde → HCID 21704983, compound

HRID 1595503Notes

Reaction equation

HRID 1595503 reaction equation
[N+](C1C=C(S([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[CH:27]=3)(=[O:25])=[O:24])=[CH:18][CH:17]=2)(=O)=O)C=CC=1)([O-])=O.O[C:36]1[CH:43]=[CH:42][C:39]([CH:40]=[O:41])=[CH:38][CH:37]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N+:32]([C:28]1[CH:27]=[C:26]([S:23]([O:22][C:19]2[CH:18]=[CH:17][C:16]([CH2:15][CH2:14][O:13][C:36]3[CH:43]=[CH:42][C:39]([CH:40]=[O:41])=[CH:38][CH:37]=3)=[CH:21][CH:20]=2)(=[O:25])=[O:24])[CH:31]=[CH:30][CH:29]=1)([O-:34])=[O:33]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 21704950HCID 21704950, compound

Product 1

HCID 21704983HCID 21704983, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 32.5 g (64 mmole) 4-([3-nitrophenylsulfonyl]oxy)phenethyl 3-nitrobenzenesulfonate, 8 g (65 mmole) p-hydroxybenzaldehyde and 20 g (145 mmole) potassium carbonate in 300 ml acetonitrile was refluxed for 10 minutes, then stirred at room temperature over night and thereafter refluxed for 30 minutes. The salts were filtered off and the solvent evaporated in vacuo. Dichloromethane and water were added, the phases were separated, the organic phase was dried and the solvent was evaporated in vacuo. Purification by chromatography on silica gel using dichloromethane as eluent and crystallization in diisopropyl ether gave 23.5 g (yield 86%) of 4-[2-(4-formylphenoxy)ethyl]phenyl 3-nitrobenzenesulfonate.

Workup

  1. temperaturewas refluxed for 10 minutes
  2. temperaturerefluxed for 30 minutes
  3. filtrationThe salts were filtered off
  4. customthe solvent evaporated in vacuo
  5. additionDichloromethane and water were added
  6. customthe phases were separated
  7. customthe organic phase was dried
  8. customthe solvent was evaporated in vacuo
  9. customPurification by chromatography on silica gel
  10. customcrystallization in diisopropyl ether

Sources & evidence

ORD record
ord-f2cf617eb4e846c29f6865e556f4b079
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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