Sulfuric Acid → 1,3-Dimethoxy-2-(3-phenylpropyl)benzene

HRID 328019

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1.C([Li])CCC.I[CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.S(=O)(=O)(O)O>O1CCCC1.CCCCCC.CCOCC.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

Reaktionsbedingungen

Temperatur: -20 °C

Versuchsvorschrift

A solution of 8.70 g (63 mmol) of 1,3-dimethoxybenzene in 164 mL of anhydrous tetrahydrofuran was stirred at -20° C. while 1.6M n-butyllithium in hexane (42.1 mL; 67.2 mmol) was added dropwise, over 20 min. The solution was stirred at -20° C. for 3 hr and then allowed to warm to -5° C. whereupon 15.66 g (63.6 mmol) of 1-iodo-3-phenylpropane was added over 15 min. The reaction mixture was stirred at -5° C. for 1 hr and then at room temperature for 3 d. After being recooled to -5° C., the reaction mixture was decomposed by the addition of 1.5N aqueous sulfuric acid. Water was added and the mixture was worked-up with ether in the usual manner. The residue was treated with 100 mL of hexane and the mixture was filtered. Removal of the solvent in vacuo gave 15.28 g (94.7%) of the title compound as a yellow oil.

Aufarbeitung

additionwas added dropwise, over 20 min
additionwas added over 15 min
stirringThe reaction mixture was stirred at -5° C. for 1 hr
waitat room temperature for 3 d
customAfter being recooled to -5° C.
filtrationthe mixture was filtered
customRemoval of the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-47b161c95d4b45279ef91e16a42220ad
Quelldatensatz: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05273999

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