Hydroquinone → (+/-)-trans-1,2-DI methoxy-4-(2-nitrocyclohex-4-enyl)benzene

HRID 365413

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[N+:11]([O-:13])=[O:12])=[CH:5][C:4]=1[O:14][CH3:15].[C:16]1([CH:23]=CC(O)=[CH:19][CH:18]=1)O.C=CC=C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:19][CH:18]=[CH:16][CH2:23][C@H:10]2[N+:11]([O-:13])=[O:12])=[CH:5][C:4]=1[O:14][CH3:15]

Participants

Conditions

Temperature: 160 °C

Procedure

50.0 g of 3,4-dimethoxy-ω-nitrostyrene and 1.0 g (9.1 mmol) of hydroquinone are suspended in 200 ml of abs. toluene and treated at -70° C. with 55.0 g (1.02 mol) of liquid 1,3-butadiene. The mixture is stirred at 160° C. for 6 days in an autoclave and then cooled. Some of the solvent is distilled off in vacuo, and the resulting precipitate is filtered off with suction and recrystallized in ethanol. M.p.: 113.5-115.5° C.; yield 76.3% of theory.

Workup

temperaturecooled
distillationSome of the solvent is distilled off in vacuo
filtrationthe resulting precipitate is filtered off with suction
customrecrystallized in ethanol

Sources & evidence

ORD record: ord-80b19b11bbcd4405bbfa02d15544a6ef
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06127378

Linked notes

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