3-Hydroxybenzaldehyde → HCID 54111600, compound

HRID 2254429Notes

Reaction equation

HRID 2254429 reaction equation
[CH2:1]([OH:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)Br.O[C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17].[H-].[Na+].C(OC(C)C)(C)C>C(OCC)C.CN(C)C=O.O>[CH2:1]([O:7][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 1013-HydroxybenzaldehydeHCID 7361Furfuryl AlcoholHCID 7914Diisopropyl EtherHCID 24614Phosphorus tribromideHCID 24758Sodium hydride

Product 1

HCID 54111600HCID 54111600, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×HCID 6228DimethylformamideSolvent

Procedure

Two grams of furfuryl alcohol was dissolved in 20 ml of anhydrous ethyl ether, and 3 ml of an anhydrous ethyl ether solution containing 2 g of phosphorus tribromide was added. The mixture was stirred for 30 minutes under ice cooling. The reaction mixture was washed with a 30% aqueous solution of sodium hydroxide, and dried over granular sodium hydroxide. The solution was then added to a previously prepared solution of 3-hydroxybenzaldehyde sodium salt (obtained by dissolving 2.44 g of 3-hydroxybenzaldehyde and 0.8 g of 60% oily sodium hydride in a mixture of 5 ml of anhydrous dimethylformamide and 10 ml of anhydrous ethyl ether), and the mixture was stirred at room temperature for 1 hour. To the reaction mixture were added isopropyl ether and water. The organic layer was separated, washed with a 10% aqueous solution of sodium hydroxide, and then dried over anhydrous sodium sulfate. The desiccant was removed by filtration, and the solvent was evaporated. The residue was purified by silica gel column chromatography (Wakogel C-200, 100 g; eluting solvent: hexane/ethyl acetate=3/1) to give 3-furfuryloxybenzaldehyde as a pale yellow oil.

Workup

  1. additionwas added
  2. washThe reaction mixture was washed with a 30% aqueous solution of sodium hydroxide
  3. dry with materialdried over granular sodium hydroxide
  4. additionThe solution was then added to a previously prepared solution of 3-hydroxybenzaldehyde sodium salt (
  5. customobtained
  6. stirringwas stirred at room temperature for 1 hour
  7. customThe organic layer was separated
  8. washwashed with a 10% aqueous solution of sodium hydroxide
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe desiccant was removed by filtration
  11. customthe solvent was evaporated
  12. customThe residue was purified by silica gel column chromatography (Wakogel C-200, 100 g; eluting solvent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-77cc032332884340a0669d462f14c1b1
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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