4-Hydroxybenzaldehyde → 4-[2-(4-Formylphenoxy)ethyl]phenyl methanesulfonate

HRID 1595492Notes

Reaction equation

HRID 1595492 reaction equation
CS([O:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][S:15]([CH3:18])(=[O:17])=[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>[CH3:18][S:15]([O:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][CH2:6][O:5][C:20]2[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=2)=[CH:9][CH:10]=1)(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 112201221-(Methylsulfonyloxy)-2-[4-(methylsulfonyloxy)phenyl]ethane

Product 1

HCID 114159454-[2-(4-Formylphenoxy)ethyl]phenyl methanesulfonateYield 66.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

30 g (0.102 mole) 4-(methylsulfonyloxy)phenethyl methanesulfonate was dissolved in acetonitrile and slowly added to a mixture of 31.1 g (0.255 mole) p-hydroxybenzaldehyde and 41.46 g (0.3 mole) potassium carbonate in acetonitrile and refluxed until the starting material was consumed. The salt was filtered off, the solvent evaporated in vacuo, dichloromethane was added and the organic phase was washed with water. After evaporation of the solvent, purification by chromatography on silica gel using dichloromethane as eluent gave 21.6 g (yield 66%) of 4-[2-(4-formylphenoxy)ethyl]phenyl methanesulfonate.

Workup

  1. temperaturerefluxed until the starting material
  2. customwas consumed
  3. filtrationThe salt was filtered off
  4. customthe solvent evaporated in vacuo, dichloromethane
  5. additionwas added
  6. washthe organic phase was washed with water
  7. customAfter evaporation of the solvent, purification by chromatography on silica gel

Sources & evidence

ORD record
ord-57485c848dd64ebd9170635e9434b74f
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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