Dichloromethane → 5-Methoxy-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene

HRID 486412

Reaktionsgleichung

Cl[C:2]([CH3:10])([CH2:4][CH2:5][C:6](Cl)([CH3:8])[CH3:7])[CH3:3].[CH3:11][C:12]1[CH:13]=[C:14]([O:18][CH3:19])C=[CH:16][CH:17]=1.Cl[CH2:21]Cl>Cl[Ti](Cl)(Cl)Cl>[CH3:3][C:2]1([CH3:10])[C:16]2[C:7](=[C:14]([O:18][CH3:19])[CH:13]=[C:12]([CH3:11])[CH:17]=2)[C:6]([CH3:21])([CH3:8])[CH2:5][CH2:4]1

Komponenten

Reaktionsbedingungen

Temperatur: 35 °C

Versuchsvorschrift

The starting material 1,1,4,4,7-pentamethyl-5-methoxy-1,2,3,4-tetrahydronaphthalene was prepared as follows. First, a 500 flask was charged with 230 ml dichloromethane, 19 g TiCl4, and 18.3 g 2,5-dichloro-2,5-dimethylhexane, at 22° C. Next, 3-methyl anisole (12.2 g in 20 ml dichloromethane) was added dropwise over a period of an hour. After the addition was completed, the solution was heated to 35° C. and the temperature maintained for an additional 2.5 hours. The solution was then cooled to 5° C. and quenched with water. After transfer to a separatory funnel, the solution was washed with water, then twice with brine, dried over anhydrous sodium sulfate, and rotary evaporated to give a crude product (23.78 g) containing 79.4% (by area % GC) of 1,1,4,4,7-pentamethyl-5-methoxy-1,2,3,4-tetrahydronaphthalene.

Aufarbeitung

additionAfter the addition
temperaturethe temperature maintained for an additional 2.5 hours
temperatureThe solution was then cooled to 5° C.
customquenched with water
washAfter transfer to a separatory funnel, the solution was washed with water
dry with materialtwice with brine, dried over anhydrous sodium sulfate
customrotary evaporated

Quellen und Nachweise

ORD-Eintrag: ord-c9fc8a668fe5448c9f1ababde1774eaf
Quelldatensatz: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05292719

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