Acetone → HCID 18761932, compound

HRID 1748701Notes

Reaction equation

HRID 1748701 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[CH:3]=1.[CH2:13](Br)[CH:14]=[CH2:15].C([O-])([O-])=O.[K+].[K+].[CH3:23][C:24]([CH3:26])=O>>[CH2:13]([O:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:26][CH:24]=[CH2:23])[CH:8]=2)[CH:3]=1)[CH:14]=[CH2:15]

Participants

5

Reactant 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 935522,6-Dihydroxynaphthalene

Product 1

HCID 18761932HCID 18761932, compound

Procedure

Into a 1,000 ml two-necked flask equipped with a refluxing condenser, 20.0 g of 2,6-dihydroxynaphthalene (Sigma-Aldrich), 27.0 ml of allyl bromide (Sigma-Aldrich), 103.61 g of K2CO3, and 500 ml of acetone are charged and mixed at room temperature. Then, the temperature was set to 80° C., and the homogeneous mixture thus obtained is refluxed overnight. After finishing the reaction, the reaction mixture is cooled to room temperature and filtered using Celite. Organic solvent is evaporated to obtain a coarse product. A target product is extracted from the coarse product using ethyl acetate, washed three times using water, and dried using MgSO4. MgSO4 is filtered off, and solvents are removed by using an evaporator to obtain an intermediate product (11), 2,6-bis(allyloxy)naphthalene. The reaction scheme of the 1st step is as follows.

Workup

  1. customInto a 1,000 ml two-necked flask equipped with a refluxing condenser
  2. additionmixed at room temperature
  3. customwas set to 80° C.
  4. customthe homogeneous mixture thus obtained
  5. temperatureis refluxed overnight
  6. customthe reaction
  7. filtrationfiltered
  8. customOrganic solvent is evaporated
  9. customto obtain a coarse product
  10. extractionA target product is extracted from the coarse product
  11. washwashed three times
  12. customdried
  13. filtrationMgSO4 is filtered off
  14. customsolvents are removed
  15. customan evaporator

Sources & evidence

ORD record
ord-576b6e9c1c414a318bc41d54e4f34dcf
Source dataset
uspto-grants-2015_10
Patent number
US09150686B2

Reaction notes

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