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

HRID 525981

Reaktionsgleichung

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]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

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

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-9909275f86894bd9a2aaf61545134d1e
Quelldatensatz: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09343198B2

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