1,5-Dihydroxynaphthalene → HCID 86724457, compound

HRID 1748698Notes

Reaction equation

HRID 1748698 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[CH:20]=[CH2:21]>CC(C)=O>[CH2:21]([O:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[CH:9][CH:8]=[C:7]2[OH:12])[CH:20]=[CH2:19]

Participants

5

Reactant 3

HCID 67491,5-DihydroxynaphthaleneHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 86724457HCID 86724457, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Into a 1,000 ml two-necked flask equipped with a refluxing condenser, 20.0 g of 1,5-dihydroxynaphthalene (Sigma-Aldrich), 51.81 g of K2CO3, and 500 ml of acetone were charged and mixed at room temperature. Then, the reaction temperature was set to 80° C., and homogeneous mixture was refluxed (hereinafter, the temperature written during the synthesis represents the set temperature of the refluxing apparatus and was higher than about 10° C. to 15° C. than true reaction temperature of reaction medium). During the refluxing, 13.5 ml of allyl bromide (Sigma-Aldrich) was added in a dropwise manner and allowed to react overnight. After finishing the reaction, the reaction mixture was cooled to room temperature and was filtered using Celite. The solvent was evaporated to obtain a coarse product. A reaction product was extracted from the coarse product using ethyl acetate, washed three times using water, and dried using MgSO4. MgSO4 was filtered off, and solvents were removed by using an evaporator to obtain an intermediate product (11), 5-(allyloxy)naphthalene-1-ol. The reaction scheme in the 1st step and the NMR data of the intermediate product (11) thus obtained are 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. temperaturehomogeneous mixture was refluxed (hereinafter, the temperature
  5. customwas higher than about 10° C. to 15° C. than true reaction temperature of reaction medium)
  6. customto react overnight
  7. customthe reaction
  8. filtrationwas filtered
  9. customThe solvent was evaporated
  10. customto obtain a coarse product
  11. extractionA reaction product was extracted from the coarse product
  12. washwashed three times
  13. customdried
  14. filtrationMgSO4 was filtered off
  15. customsolvents were removed
  16. customan evaporator

Sources & evidence

ORD record
ord-a68d8922df6845e89425d0035dde30c9
Source dataset
uspto-grants-2015_10
Patent number
US09150686B2

Reaction notes

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