2,6-Dihydroxyanthraquinone → 2,6-Bis((2-ethylhexyl)oxy)anthracene-9,10-dione

HRID 2268697

Reaction equation

[OH:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([OH:17])[CH:10]=3)[C:5](=[O:18])[C:4]=2[CH:3]=1.[CH2:19]([CH:21]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:22]Br)[CH3:20].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:19]([CH:21]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:22][O:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:17][CH2:5][CH:4]([CH2:13][CH3:12])[CH2:3][CH2:2][CH2:15][CH3:14])[CH:10]=3)[C:5](=[O:18])[C:4]=2[CH:3]=1)[CH3:20]

Participants

Conditions

Temperature: 90 °C

Procedure

2,6-Dihydroxyanthraquinone (100.0 g, 0.42 mol) and 2-ethylhexyl bromide (165.0 g, 0.86 mol) were dissolved in 1 L of DMF. To this solution was added anhydrous K2CO3 (120.0 g, 0.87 mol). The reaction was heated at 90° C. overnight. Most of DMF was removed and 500 mL of water was added. The reaction was extracted with ether (3×400 mL), washed with brine (1×200 mL), and dried over MgSO4. Solvent was removed and the crude product was recrystallized from methanol to give yellow powdery product 125.21 g (65% yield). 1H NMR (CDCl3) δ (ppm): 0.92-0.98 (m, 12H, CH3), 1.34-1.54 (m, 16H), 1.75-1.81 (m, 2H, CH(CH3)), 4.02 (d, J=5.5 Hz, 4H, OCH2), 7.19 (d, J=8.4 Hz, 2H), 7.70 (s, 2H), 8.19 (d, J=8.5 Hz, 2H); 13C NMR (CDCl3): 11.12, 14.06, 23.04, 23.88, 29.08, 30.51, 39.34, 71.34, 110.64, 120.84, 127.00, 129.62, 135.88, 164.29, 182.27. M.p. 49-51° C.; FD-MS: m/z 464 (M+).

Workup

customMost of DMF was removed
addition500 mL of water was added
extractionThe reaction was extracted with ether (3×400 mL)
washwashed with brine (1×200 mL)
dry with materialdried over MgSO4
customSolvent was removed
customthe crude product was recrystallized from methanol

Sources & evidence

ORD record: ord-6f1716f00107489991e7202869644e72
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329086B1

Linked notes

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