1,5-Dihydroxynaphthalene → 1,5-Bis(octyloxy)naphthalene

HRID 525981

Reaction equation

HRID 525981 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.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[C:22](=[O:25])([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:14]([O:12][C:7]1[C:6]2[C:11](=[C:2]([O:25][CH2:22][CH2:10][CH2:11][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH:3]=[CH:4][CH:5]=2)[CH:10]=[CH:9][CH:8]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 67491,5-DihydroxynaphthaleneHCID 81401-BromooctaneHCID 11430Potassium Carbonate

Product 1

HCID 509011751,5-Bis(octyloxy)naphthaleneYield 140.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

1,5-dihydroxynaphthalene (2.95 g, 18.4 mmol), 1-bromooctane (8.2 g, 42.5 mmol), and potassium carbonate (50 g, 0.36 mol) was mixed in N,N-dimethylformamide and heated at 90° C. for 5 h. The potassium carbonate was filtered off and the reaction mixture was quenched with water and extracted two times with ether. The combined organic phase was then washed once with 1M HCl, two times with water, and evaporated. The residual brown solid was recrystallised in ethanol to form 1,5-bis(octyloxy)naphthalene (4.96 g, 12.9 mmol) as brown crystals. 1H-NMR (CDCl3, δ): 0.89 (t, 6H), 1.2-1.4 (m, 16H), 1.4-1.6 (m, 4H), 1.91 (m, 4H), 4.12 (t, 4H), 6.81 (d, 2H), 7.34 (t, 2H), 7.83 (d, 2H) MS MALDI-TOF (m/z): 384.266

Workup

  1. filtrationThe potassium carbonate was filtered off
  2. customthe reaction mixture was quenched with water
  3. extractionextracted two times with ether
  4. washThe combined organic phase was then washed once with 1M HCl, two times with water
  5. customevaporated
  6. customThe residual brown solid was recrystallised in ethanol

Sources & evidence

ORD record
ord-9909275f86894bd9a2aaf61545134d1e
Source dataset
uspto-grants-2016_05
Patent number
US09343198B2

Linked notes

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