4-Hydroxybenzaldehyde → HCID 21705012, compound

HRID 1595488Notes

Reaction equation

HRID 1595488 reaction equation
COC1C=CC(S([O:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][S:22]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)(=[O:24])=[O:23])=[CH:17][CH:16]=2)(=O)=O)=CC=1.O[C:34]1[CH:41]=[CH:40][C:37]([CH:38]=[O:39])=[CH:36][CH:35]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:32][O:31][C:28]1[CH:29]=[CH:30][C:25]([S:22]([O:21][C:18]2[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][O:12][C:34]3[CH:41]=[CH:40][C:37]([CH:38]=[O:39])=[CH:36][CH:35]=3)=[CH:16][CH:17]=2)(=[O:24])=[O:23])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 21705015HCID 21705015, compound

Product 1

HCID 21705012HCID 21705012, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 8.5 g (17.8 mmole) 4-(4-methoxyphenylsulfonyloxy)phenethyl 4-methoxy-1-benzenesulfonate, 2.16 g (17.7 mmole) 4-hydroxybenzaldehyde and 10 g (72.5 mmole) potassium carbonate in 60 g acetonitrile was refluxed over night. The salt was filtered off and the solvent was evaporated. The crude product was purified on silica gel using dichloromethane as eluent to give 7.4 g of 4-[2-(4-formylphenoxy)ethyl]phenyl 4-methoxy-1-benzenesulfonate (slightly polluted with the corresponding styrene product).

Workup

  1. temperaturewas refluxed over night
  2. filtrationThe salt was filtered off
  3. customthe solvent was evaporated
  4. customThe crude product was purified on silica gel

Sources & evidence

ORD record
ord-f6535b4b1fc84eca822fb390ec24d1cc
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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