Reaktion #737759

Reaktionsgleichung

water

1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydro-naphthalene

acetyl chloride

AlCl3

→

title compound

1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   SonstigeThe organic phase was separated
3. 3
   Extraktionthe water phase was further extracted with methylene chloride (3×30 ml)
4. 4
   WaschenThe combined organic phases were first washed with brine
5. 5
   Sonstigethen dried
6. 6
   Sonstigebefore evaporated
7. 7
   SonstigeThe residue was purified by column chromatography

Vorschrift

To a suspension of AlCl3 (2.88 g; 21.6 mmol) in methylene chloride (5 ml) was added over 15 minutes a solution of 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydro-naphthalene (4.0 g; 20 mmol) and acetyl chloride (1.6 ml; 21.6 mmol) in methylene chloride (20 ml) at 0° C. The reaction mixture was stirred for 30 minutes and ice cooled water (50 ml) was added. The organic phase was separated and the water phase was further extracted with methylene chloride (3×30 ml). The combined organic phases were first washed with brine then dried before evaporated. The residue was purified by column chromatography using hexane:methylene chloride (1:1) to give the title compound in 4.9 g (100%) yield.

Quelle