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

HRID 2093237Notes

Reaction equation

HRID 2093237 reaction equation
C([O-])([O-])=O.[K+].[K+].[OH:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([OH:16])[CH:15]=1)[CH2:11][OH:12].[CH2:17](Cl)[C:18]#[CH:19].[CH3:21][C:22]([CH3:24])=O>>[CH2:17]([O:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([O:16][CH2:24][C:22]#[CH:21])[CH:15]=1)[CH2:11][OH:12])[C:18]#[CH:19]

Participants

5

Reactant 4

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

Product 1

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

Procedure

Finely powdered K2CO3 (14 g, 0.10 mol), and KI (17 g, 0.10 mol) were stirred in acetone (200 mL) under a nitrogen atmosphere. 3,5-Dihydroxybenzyl alcohol (4.2 g, 0.030 mol), and propargyl chloride (5.3 g, 0.071 mol) were added and mixture was allowed to reflux overnight. After the solution was filtered, and evaporated down to dryness, the residue was diluted with DCM, worked up and the solvents were removed in vacuo leaving a yellow oil, which solidified upon standing to give 6.3 g in 97% yield.

Workup

  1. temperatureto reflux overnight
  2. filtrationAfter the solution was filtered
  3. customevaporated down to dryness
  4. additionthe residue was diluted with DCM
  5. customthe solvents were removed in vacuo
  6. customleaving a yellow oil, which
  7. customto give 6.3 g in 97% yield

Sources & evidence

ORD record
ord-77645c87f455494b81cc4c2f2a45205c
Source dataset
uspto-grants-2013_05
Patent number
US08444953B2

Reaction notes

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