o-Chloranil → 6-methoxy-1-methylnaphthalene

HRID 1007138Notes

Reaction equation

HRID 1007138 reaction equation
ClC1C(=O)C(=O)C(Cl)=C(Cl)C=1Cl.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]([CH3:25])[CH2:20][CH:19]=[CH:18]2>C(OCC)C>[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:21]([CH3:25])=[CH:20][CH:19]=[CH:18]2

Participants

4

Reactant 2

HCID 73252o-ChloranilHCID 22667820HCID 22667820, compound

Product 1

HCID 102196186-methoxy-1-methylnaphthaleneYield 53%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Tetrachloro-1,2-benzoquinone (3.6 g, 14.5 mmol) was added in one portion to a stirred solution of 6-methoxy-1-methyl-1,2-dihydronaphthalene (2.3 g, 13.2 mmol) in diethyl ether (20 ml). The reaction was concetrated down after 24h and purified by column chromatography using petroleum ether as eluent to gave the title compound as a white solid (1.2 g, 53%). 1H-NMR (250 MHz, CDCl3) 2.5 (s, 3H), 3.8 (s, 3H), 7.0-7.8 (m, 6H), 13C-NMR (250 MHz, CDCl3) 19.3, 55.2, 106.5, 118.1, 124.4, 125.2, 125.7, 126.2, 128.0, 134.2. 134.7, 157.3; Mass Spectrum (M+1) m/e=173.

Workup

  1. custompurified by column chromatography

Sources & evidence

ORD record
ord-782240f851a440fa82b5a82f01884916
Source dataset
uspto-grants-2004_09
Patent number
US06794384B1

Reaction notes

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