Acetone → [3-methoxy-4-(2-propynyloxy)phenyl]methanol

HRID 890334Notes

Reaction equation

HRID 890334 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH3:7][C:8]([CH3:10])=O.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[OH:21])[CH2:16][OH:17].C(Cl)C#C>ClCCl>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][CH2:10][C:8]#[CH:7])[CH2:16][OH:17]

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 122213-Chloro-1-propyneHCID 62348Vanillyl alcohol2×

Product 1

HCID 2763324[3-methoxy-4-(2-propynyloxy)phenyl]methanolYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Finely powdered K2CO3, 10.4 grams (0.075 moles), and KI, 9.1 grams (0.060 moles), were placed in a 300 mL round-bottomed flask equipped with a magnetic stir bar, and 150 mL acetone was added. 3-methoxy-4-hydroxybenzyl alcohol, 7.71 grams (0.050 moles), and propargyl chloride, 4.10 grams (0.055 moles), were then added, and the mixture stirred and refluxed for approximately 48 hours. The results from thin layer chromatography showed no starting material (3-methoxy-4-hydroxybenzyl alcohol) as well as the presence of a new compound. The solution was then filtered. The acetone of the resulting filtrate was removed by rotary evaporation, leaving an oily residue. The oily residue was dissolved in 50 mL dichloromethane and washed with water (30 mL×2) and then dried over anhydrous potassium carbonate. After filtering the organic phase, the solvents were removed by rotary evaporation, leaving a liquid product. 9 grams of product was obtained, which corresponds to a 94% yield.

Workup

  1. customequipped with a magnetic stir bar
  2. temperaturerefluxed for approximately 48 hours
  3. customThe results from thin layer chromatography
  4. filtrationThe solution was then filtered
  5. customThe acetone of the resulting filtrate was removed by rotary evaporation
  6. customleaving an oily residue
  7. washwashed with water (30 mL×2)
  8. dry with materialdried over anhydrous potassium carbonate
  9. filtrationAfter filtering the organic phase
  10. customthe solvents were removed by rotary evaporation
  11. customleaving a liquid product

Sources & evidence

ORD record
ord-a41dc7d87f7549e1a6ff908c7375c10d
Source dataset
uspto-grants-2006_02
Patent number
US06995260B2

Reaction notes

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