Reacción #41218

Ecuación de reacción

dichloromethane

4,5-Dihydroxy-9,10-dioxoanthracene-2-carboxylic acid

Benzyloxyacetyl chloride

water

ethyl acetate

→

4,5-Bis(2-benzyloxyacetyloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto give a clear reaction mixture which
2. 2
   workup.STIRRINGwas stirred at RT over the weekend
3. 3
   Otroquenched with 2M HCl (200 ml)
4. 4
   OtroAn orange solid was isolated by filtration
5. 5
   OtroA yellow solid was isolated by filtration (3.6 g, 61%)

Procedimiento

4,5-Dihydroxy-9,10-dioxoanthracene-2-carboxylic acid (3.0 g) was suspended in pyridine (100 ml) and stirred at RT for 30 mins. Benzyloxyacetyl chloride (3.6 g, 5 equiv.) was added, to give a clear reaction mixture which was stirred at RT over the weekend. The reaction mixture was reduced to a smaller volume and quenched with 2M HCl (200 ml), adjusting the pH to pH 2. An orange solid was isolated by filtration. This crude solid was slurried in water (30 ml), followed by ethyl acetate (30 ml) and dichloromethane (30 ml). A yellow solid was isolated by filtration (3.6 g, 61%).

Fuente