Reaktion #345499

Reaktionsgleichung

2-chloro-9-formylanthracene

2-chloro-9-formylanthracene

vinyl acetate

→

title compound

12-Acetoxy-2-chloro-9-formyl-9,10-dihydro-9,10-ethanoanthracene

Lösungsmittel

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled
2. 2
   EinengenThe reaction mixture was concentrated on the rotary evaporator
3. 3
   Sonstigeto remove the excess vinyl acetate
4. 4
   Sonstigeleaving the crude product as a tan crystalline solid
5. 5
   Filtrationwas collected by filtration
6. 6
   Waschenwashed with diethyl ether (2×300 ml)
7. 7
   Sonstigevacuum dried

Vorschrift

A mixture of 2-chloro-9-formylanthracene (described in Example 1b) (100.0 g, 0.415 mol) and vinyl acetate (400 ml, 374 g, 4.34 mol) was placed in a stainless steel bomb (PARR) and heated at 200° C. (sand bath temp.) for 24 h, then cooled. The reaction mixture was concentrated on the rotary evaporator to remove the excess vinyl acetate, leaving the crude product as a tan crystalline solid. The crude product from several batches, which consumed 670.0 g (2.78 mol) of the 2-chloro-9-formylanthracene, was pooled. Trituration with diethyl ether (1.0 L) gave an off-white crystalline solid which was collected by filtration, washed with diethyl ether (2×300 ml), then vacuum dried to afford 629.0 g (69.1%) of the title compound (mp 145°-153° C.). NMR (CDCl3) 10.58 (s) and 10.64 (s, 1H), 7.63 (m) and 7.76 (d, J=1.5 Hz, 1H), 7.15-7.36 (m, 6H), 5.46 (m, 1H), 4.29 (s, 1H), 2.55 (m, 1H), 1.88 (s) and 1.91 (s, 1H), 1.55 (m, 1H)

Quelle