Salicyl Alcohol → HCID 17958622, compound

HRID 2110253Notes

Reaction equation

HRID 2110253 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[C:10]1([C:16]2[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:16]1([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:17]=[CH:18][C:19]([CH2:20][O:1][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH2:4][OH:5])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 5146Salicyl AlcoholHCID 11430Potassium CarbonateHCID 154634-Phenylbenzyl chloride

Product 1

HCID 17958622HCID 17958622, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2.92 g (23.49 mmol) of 2-hydroxybenzyl alcohol, 5.00 g (24.67 mmol) of 4-phenylbenzyl chloride and 3.41 g (24.67 mmol) of potassium carbonate in 60 ml of acetone was heated at reflux overnight. The precipitate formed was filtered off. The residue was taken up in 1N NaOH, and the mixture was extracted with ethyl acetate. The combined organic phases were dried over Na2SO4 and the solvent was removed. The product was purified chromatographically (silica gel, cyclohexane/ethyl acetate 10:1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customThe precipitate formed
  4. filtrationwas filtered off
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. customthe solvent was removed
  8. customThe product was purified chromatographically (silica gel, cyclohexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-76bdf3fca3a2419b9f64184a39cb4ef4
Source dataset
uspto-grants-2009_04
Patent number
US07517896B2

Reaction notes

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