Acetic Acid → 1,1,4,4,6-Pentamethyl-7-nitro-1,2,3,4-tetrahydronaphthalene

HRID 981003

Reaktionsgleichung

[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8]([CH3:13])([CH3:12])[CH2:7][CH2:6][C:5]([CH3:15])([CH3:14])[C:4]=2[CH:3]=1.[N+:16]([O-])([OH:18])=[O:17].C(O)(=O)C>C(OC(=O)C)(=O)C>[CH3:1][C:2]1[C:11]([N+:16]([O-:18])=[O:17])=[CH:10][C:9]2[C:8]([CH3:13])([CH3:12])[CH2:7][CH2:6][C:5]([CH3:15])([CH3:14])[C:4]=2[CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

50 g (250 mmoles) of 2-methyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl naphthalene are dissolved in 200 ml of acetic anhydride. The solution is cooled to 0° C. and there is slowly added a solution of 10.5 ml (250 mmoles) of nitric acid, 20 ml of acetic acid and 20 ml of acetic anhydride, while maintaining the temperature between 0° and 5° C. The reaction mixture is then stirred for 1 hour at ambient temperature, poured into ice water and filtered. The resulting solid is washed with water. The solid is dissolved in methylene chloride, washed with water and then with a saturated solution of sodium bicarbonate, dried on MgSO4 and evaporated. 45.8 g (74%) of 2-methyl-3-nitro-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl naphthalene which melts at 143°-144° C. are obtained.

Aufarbeitung

temperaturewhile maintaining the temperature between 0° and 5° C
filtrationfiltered
washThe resulting solid is washed with water
dissolutionThe solid is dissolved in methylene chloride
washwashed with water
dry with materialwith a saturated solution of sodium bicarbonate, dried on MgSO4
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-8e58f11d9ced48d3935807601ec4c0ee
Quelldatensatz: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: USRE033533

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