4-Hydroxybenzaldehyde → HCID 21704994, compound

HRID 1595540Notes

Reaction equation

HRID 1595540 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])=[C:10]([O:19][CH3:20])[CH:9]=1)(=O)=O.O[C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=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:22]2[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=2)=[CH:9][C:10]=1[O:19][CH3:20])(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 21704982HCID 21704982, compound

Product 1

HCID 21704994HCID 21704994, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

50 g (0.154 mole) 3-methoxy-4-(methylsulfonyloxy)phenethyl methanesulfonate, 48.8 g 0.4 mole) p-hydroxybenzaldehyde, 65.45 g 0.473 mole) potassium carbonate in 500 ml acetonitrile was refluxed for 4 hours. The precipitate was filtered off and the solvent was evaporated. Dichloromethane was added and the organic phase was washed with water, dried (magnesium sulfate), filtered and the solvent was evaporated to give 34 g (yield 63%) of 4-[2-(4-formylphenoxy)ethyl]-2-methoxyphenyl methanesulfonate.

Workup

  1. filtrationThe precipitate was filtered off
  2. customthe solvent was evaporated
  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-f8bcccb944aa4ff198d0ca22c0e8a285
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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