Phenol → 1,2-Dihydro-4-[6-(phenyloxy)hexyloxy]-1,2-dioxonaphthalene
Reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.I[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][C:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:37](=[O:44])[C:36](=[O:45])[CH:35]=1>CN(C=O)C>[C:1]1([O:7][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][C:34]2[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37](=[O:44])[C:36](=[O:45])[CH:35]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
Procedure
Phenol (28 mg, 0.3 mmol) was treated with tetrabutylammonium hydroxide (0.3 mL of 1.0 M solution in methanol) and the reaction mixture was concentrated to dryness in vacuo. Iodonaphtoquinone 5 (115 mg, 0.3 mmol) in DMF (3 mL) was added to the tetrabutylammonium salt, stirred for 48 h and quenched with H2O (10 mL). The product was extracted with CHCl3, the extract was washed with H2O, then brine, dried (Na2SO4), and purified by chromatography (5% EtOAc in benzene) to give 12 as a yellow solid (45 mg, 43%) 1H NMR (CDCl3) 8.13 (d, J=7.4 Hz, 1H), 7.86 (d, J=7.4 Hz, 1H), 7.67 (t, J=7.6 Hz, 1H), 7.61 (t, J=7.5 Hz, 1H), 7.15-7.40 (m, 2H), 6.85-7.10 (m, 3H), 5.96 (s, 1H), 4.17 (t, J=6.5 Hz, 2H), 3.99 (t, J=6.2 Hz), 1.70-2.10 (m, 4H), 1.35-1.70 (m, 4H).
Workup
- concentrationthe reaction mixture was concentrated to dryness in vacuo
- customquenched with H2O (10 mL)
- extractionThe product was extracted with CHCl3
- washthe extract was washed with H2O
- dry with materialbrine, dried (Na2SO4)
- custompurified by chromatography (5% EtOAc in benzene)
Sources & evidence
- ORD record
- ord-1c41d2402a384af3ad514507ab10377e
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06809176B2
Reaction notes
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