4-Hydroxybenzaldehyde → HCID 21704999, compound

HRID 1595544Notes

Reaction equation

HRID 1595544 reaction equation
CS([O:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][S:15]([CH3:18])(=[O:17])=[O:16])[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:10]1[CH:11]=[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]=1)(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 21704987HCID 21704987, compound

Product 1

HCID 21704999HCID 21704999, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

9.3 g (31.6 mmole) 3-(methylsulfonyloxy)phenethyl methanesulfonate, 9.91 g (82 mmole) p-hydroxybenzaldehyde and 13 g (94.8 mmole) potassium carbonate in 200 ml acetonitrile were refluxed for 4 hours. The precipitate was filtered off and the solvent was evaporated in vacuo. Dichloromethane was added and the organic phase was washed with water, dried (magnesium sulfate), filtered and the solvent was evaporated to give 8.72 g (yield 88%) of 3-[2-(4-formylphenoxy)ethyl]phenyl methanesulfonate.

Workup

  1. filtrationThe precipitate was filtered off
  2. customthe solvent was evaporated in vacuo
  3. additionDichloromethane was added
  4. washthe organic phase was washed with water
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c8193f6f6db443898795a35b4817b283
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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