4-Hydroxybenzaldehyde → HCID 21704979, compound

HRID 1595530Notes

Reaction equation

HRID 1595530 reaction equation
C1(S([O:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:22])=[O:21])=[CH:15][CH:14]=2)(=O)=O)C=CC=CC=1.O[C:30]1[CH:37]=[CH:36][C:33]([CH:34]=[O:35])=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:23]1([S:20]([O:19][C:16]2[CH:15]=[CH:14][C:13]([CH2:12][CH2:11][O:10][C:30]3[CH:37]=[CH:36][C:33]([CH:34]=[O:35])=[CH:32][CH:31]=3)=[CH:18][CH:17]=2)(=[O:21])=[O:22])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 21704973HCID 21704973, compound

Product 1

HCID 21704979HCID 21704979, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

20 g (48 mmole) 4-[phenylsulfonyloxy]phenethyl 1-benzenesulfonate, 11.7 g (95 mmole) p-hydroxybenzaldehyde and 13.27 g (96 mmole) potassium carbonate in 100 ml acetonitrile were refluxed over night. The precipitate was filtered off and the filtrate was evaporated in vacuo. Dichloromethane was added, the solid material was filtered off and the filtrate was evaporated in vacuo. The residue was purified by chromatography on silica gel using ethyl acetate:petroleum ether (1:2) as eluent to give 12 g (yield 65%) of 4-[2-(4-formylphenoxy)ethyl]phenyl 1-benzenesulfonate.

Workup

  1. filtrationThe precipitate was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. additionDichloromethane was added
  4. filtrationthe solid material was filtered off
  5. customthe filtrate was evaporated in vacuo
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-9e667af758634160aa142b0acb6f6c73
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

Loading…