Acetone → {3,5-Bis[(prop-2-yn-1-yl)oxy]phenyl}methanol

HRID 1611805Notes

Reaction equation

HRID 1611805 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH3:7][C:8]([CH3:10])=O.[OH:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([OH:20])[CH:19]=1)[CH2:15][OH:16].[CH2:21](Cl)[C:22]#[CH:23]>ClCCl>[CH2:7]([O:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([O:20][CH2:23][C:22]#[CH:21])[CH:19]=1)[CH2:15][OH:16])[C:8]#[CH:10]

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 122213-Chloro-1-propyneHCID 346613,5-Dihydroxybenzyl alcohol2×

Product 1

HCID 15203944{3,5-Bis[(prop-2-yn-1-yl)oxy]phenyl}methanolYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Finely powdered K2CO3, 14 grams (0.10 moles), and Kl, 17 grams (0.10 moles) were placed in a 500 mL round flask, and 200 mL acetone was added. Under a nitrogen atmosphere, 3,5-dihydroxybenzylalcohol, 4.2 grams (0.03 moles), and propargyl chloride, 5.3 grams (0.07 moles) were then added. The resulting mixture was refluxed overnight. The results from thin layer chromatography showed no starting material (3,5-dihydroxybenzylalcohol) as well as the presence of a new compound. The solution was filtered, and the filtered solid washed with acetone. The acetone of the resulting filtrate was removed by rotary evaporation, leaving an organic residue. Dichloromethane (50 mL) was added to dissolve the organic residue, and this was washed with water (30 mL×2), and then dried over anhydrous sodium sulfate. After filtering the organic phase, the solvents were removed by rotary evaporation leaving a yellow oil, which solidified upon standing. 6.3 g of product was obtained, which corresponds to a 97% yield.

Workup

  1. temperatureThe resulting mixture was refluxed overnight
  2. customThe results from thin layer chromatography
  3. filtrationThe solution was filtered
  4. washthe filtered solid washed with acetone
  5. customThe acetone of the resulting filtrate was removed by rotary evaporation
  6. customleaving an organic residue
  7. dissolutionto dissolve the organic residue
  8. washthis was washed with water (30 mL×2)
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationAfter filtering the organic phase
  11. customthe solvents were removed by rotary evaporation
  12. customleaving a yellow oil, which

Sources & evidence

ORD record
ord-ce9a3f48da3940bcbba09dff3003a685
Source dataset
uspto-grants-2006_01
Patent number
US06989443B2

Reaction notes

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