Acetone → HCID 3706636, compound

HRID 2406830Notes

Reaction equation

HRID 2406830 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]2[O:6][CH2:7][O:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:17][C:18]([CH3:20])=O.C(Br)C#C>C1(C)C=CC=CC=1>[CH2:20]([O:1][C:2]1[CH:10]=[CH:9][C:5]2[O:6][CH2:7][O:8][C:4]=2[CH:3]=1)[C:18]#[CH:17]

Participants

6

Reactant 4

HCID 180AcetoneHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 68289Sesamol

Product 1

HCID 3706636HCID 3706636, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 12.9 g (0.092 moles) of 5-hydroxy-benzo[1.3]dioxole, 13.0 g (0.092 moles) of anhydrous potassium carbonate in ml 30 of acetone was added with 13.7 g (0.092 moles) of a solution of propargyl bromide in toluene (80% w/w) and the mixture was heated to reflux for 4 hrs. The mixture was then cooled to room temperature, filtered and the filtrate evaporated u.v (20 ° C./ 21 mbar). The residue was purified on silica gel column (eluant n-hexane: isopropyl ether 95: 5 v/v). A liquid product (13.6 g, 95.6% purity) was obtained whose NMR and MS analyses correspond to those of the aforementioned compound is obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hrs
  3. filtrationfiltered
  4. customthe filtrate evaporated u.v (20 ° C./ 21 mbar)
  5. customThe residue was purified on silica gel column (eluant n-hexane: isopropyl ether 95: 5 v/v)
  6. customA liquid product (13.6 g, 95.6% purity) was obtained whose NMR and MS analyses
  7. customis obtained

Sources & evidence

ORD record
ord-f26acad150bc4cab9f4a43657f971a9b
Source dataset
uspto-grants-2014_08
Patent number
US08809389B2

Reaction notes

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