4-Hydroxybenzaldehyde → HCID 21705020, compound

HRID 1595520Notes

Reaction equation

HRID 1595520 reaction equation
CS([O:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:9]=1)(=O)=O.O[C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:24]([C:23]1[CH:26]=[CH:27][C:20]([O:5][CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:16])[O:17][CH3:18])=[CH:10][CH:9]=2)=[CH:21][CH:22]=1)=[O:25]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 21704971HCID 21704971, compound

Product 1

HCID 21705020HCID 21705020, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7 g (26 mmole) 4-[(methoxycarbonyl)amino]phenethyl methanesulfonate, 6.2 g (51 mmole) 4-hydroxybenzaldehyde and 7.05 g potassium carbonate in acetonitrile was refluxed for 3 h. The solvent was evaporated in vacuo, 1 M sodium hydroxide was added and the product was extracted with dichloromethane, washed with brine, dried and the solvent was evaporated. The reaction was not completed and therfore restarted with 3.1 g 4-hydroxybenzaldehyde and 3.5 g potassium carbonate in acetonitrile and refluxed for 4 h. The solvent was evaporated and the residue was stirrred in dichloromethane over night. The precipitate was filtered off and the solvent was evaporated to give 5.9 g (yield 75.8%) of methyl N-{4-[2-(4-formylphenoxy)ethyl]phenyl}carbamate wich was used without further purification.

Workup

  1. customThe solvent was evaporated in vacuo, 1 M sodium hydroxide
  2. additionwas added
  3. extractionthe product was extracted with dichloromethane
  4. washwashed with brine
  5. customdried
  6. customthe solvent was evaporated
  7. temperaturerefluxed for 4 h
  8. customThe solvent was evaporated
  9. waitthe residue was stirrred in dichloromethane over night
  10. filtrationThe precipitate was filtered off
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c8dd763fbe6b42c38e9a0ee57d9fbd13
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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