Veratrole → 6,7-dimethoxy-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene

HRID 1499985Notes

Reaction equation

Cl[C:2]([CH3:10])([CH2:4][CH2:5][C:6](Cl)([CH3:8])[CH3:7])[CH3:3].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20].[Al+3].[Cl-].[Cl-].[Cl-]>ClCCCl>[CH3:11][O:12][C:13]1[CH:18]=[C:17]2[C:16](=[CH:15][C:14]=1[O:19][CH3:20])[C:6]([CH3:8])([CH3:7])[CH2:5][CH2:4][C:2]2([CH3:10])[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

2,5-dichloro-2,5-dimethylhexane (2.2 g, 12 mmol), 1,2-dimethoxybenzene (1.38 g, 10 mmol), anhydrous 1,2-dichloroethane (10 mL) and anhydrous AlCl3 (200 mg) were combined in a 100 mL Schlenk flask under Ar. The mixture was heated at 60° C. for 6 h before quenching with ice water. The layers were then separated, and the aqueous layer extracted three times with CH2Cl2. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The remaining residue was purified by flash column chromatography (hexanes/Ethyl acetate=10:1) to afford the title compound (1.1 g, 35% yield). 1H NMR (CDCl3): 1.27 (s, 12H), 1.67 (s, 4H), 3.86 (s, 6H), 6.77 (s, 2H); 13C NMR (CDCl3): 32.07, 34.22, 35.42, 56.01, 109.37, 137.23, 147.05.

Workup

custombefore quenching with ice water
customThe layers were then separated
extractionthe aqueous layer extracted three times with CH2Cl2
washThe combined organic layers were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe remaining residue was purified by flash column chromatography (hexanes/Ethyl acetate=10:1)

Sources & evidence

ORD record: ord-175c7d5031674ba6ba251053a6417e3a
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09203112B2

Reaction notes

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