Water → HCID 67387610, compound

HRID 2066378Notes

Reaction equation

HRID 2066378 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:12].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O.C(OCC)(=O)C>[CH2:13]([O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 113181,2-DihydroxynaphthaleneHCID 11430Potassium Carbonate

Product 1

HCID 67387610HCID 67387610, compoundYield 18.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

1,2-Dihydroxynaphthalene (70 mg) was dissolved in acetone (1 ml), the solution was added with benzyl bromide (74.7 mg) and potassium carbonate (72.5 mg), and the mixture was stirred at 70° C. for 1 hour. The reaction mixture was added with distilled water and ethyl acetate, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine=50:10:0.2) to obtain the title compound (20.7 mg).

Workup

  1. customthe layers were separated
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (hexane:acetone:triethylamine=50:10:0.2)

Sources & evidence

ORD record
ord-50318c999f944bf1960f183bc0f4f14b
Source dataset
uspto-grants-2012_10
Patent number
US08293715B2

Reaction notes

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