Reaction #2006442

Reaction equation

2-(2-aminoethoxy)ethanol

9-anthracenemethanol

4-nitrophenyl chloroformate

triethylamine

→

[2-(2-Hydroxy-ethoxy)-ethyl]-carbamic acid anthracen-9-ylmethyl ester

Solvents

CH2Cl2

CH2Cl2

Conditions

Workup

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for another 24 hours
3. 3
   Washwas then washed with a 2% sodium hydroxide (w/w) solution until no p-nitrophenol
4. 4
   DryingThe dichloromethane was dried with sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated under reduced pressure

Procedure

To a stirring slurry of 9-anthracenemethanol (10 g, 48 mmol) and 4-nitrophenyl chloroformate (13.6 g, 67.5 mmol) in 200 ml CH2Cl2 was added triethylamine (6.7 ml, 0.19 mol). The resulting gold colored solution was allowed to stir 16 hrs at room temperature. At this point, 2-(2-aminoethoxy)ethanol (14.4 ml, 0.144 mol) was added and stirring continued for another 24 hours. The CH2Cl2 reaction mixture was then washed with a 2% sodium hydroxide (w/w) solution until no p-nitrophenol was observed in the organic layer. The dichloromethane was dried with sodium sulfate, filtered, and evaporated under reduced pressure.

Source