1,5-Dihydroxynaphthalene → 1,5-Bis-(2-ethylhexyloxy)naphthalene

HRID 590901

Reaction equation

HRID 590901 reaction equation
O[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:13](=[O:16])([O-])[O-].[K+].[K+].[CH2:19]([CH:21]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:22]Br)[CH3:20]>CN(C)C=O>[CH2:19]([CH:21]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:22][O:12][C:7]1[C:6]2[C:11](=[C:2]([O:16][CH2:13][CH:2]([CH2:11][CH3:10])[CH2:3][CH2:4][CH2:5][CH3:6])[CH:3]=[CH:4][CH:5]=2)[CH:10]=[CH:9][CH:8]=1)[CH3:20]

Participants

5

Reactant 3

HCID 67491,5-DihydroxynaphthaleneHCID 11430Potassium CarbonateHCID 868042-Ethylhexyl bromide

Product 1

HCID 709804481,5-Bis-(2-ethylhexyloxy)naphthaleneYield 133.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.0 g of 1,5-dihydroxynaphthalene (31.2 mmol) and 43.1 g of potassium carbonate (311 mmol) were dissolved in 50 mL of dimethylformamide (DMF). 18.0 g of 2-ethylhexyl bromide (93.2 mmol) was added thereto and stirred at 1000 for 24 hours. After the mixture was quenched with water, extracted with ethylacetate, and sequentially washed with water and salt water, excess water was removed using magnesium sulfate, followed by column chromatography, thereby obtaining 8.0 g of the title compound (66.6%).

Workup

  1. customAfter the mixture was quenched with water
  2. extractionextracted with ethylacetate
  3. washsequentially washed with water and salt water, excess water
  4. customwas removed

Sources & evidence

ORD record
ord-ee8e50b784ce4b5c8f95386e4ee31b1d
Source dataset
uspto-grants-2016_01
Patent number
US09236573B2

Linked notes

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