Reaction #640554

Reaction equation

9,10-bis(chloromethyl)anthracene

NaH

N-methylethanolamine

→

anthracene

Yield 101.0%

Solvents

DMF

DMF

Conditions

Workup

1. 1
   workup.ADDITIONAfter addition
2. 2
   TemperatureThe resulting mixture was heated to −10° C. after a lapse of one hour
3. 3
   workup.ADDITIONfrom the completion of this addition
4. 4
   workup.STIRRINGstirred over one night
5. 5
   workup.DISTILLATIONwas distilled off under a reduced pressure
6. 6
   workup.DISSOLUTIONthe residue was dissolved in 200 ml of methylene chloride
7. 7
   Filtrationinsoluble matter was filtered out
8. 8
   workup.ADDITION50 ml of water was added to this, and TFA
9. 9
   workup.ADDITIONwas added
10. 10
    workup.STIRRINGwhile stirring until the pH of the solution
11. 11
    OtherAfter leaving at rest for 15 minutes
12. 12
    Otherthe solution was separated into two layers
13. 13
    ConcentrationA water phase was concentrated
14. 14
    Dryingthe water phase was freeze-dried

Procedure

That is, 2.06 g (27.0 mmol) of N-methylethanolamine was dissolved in 90 ml of anhydrous DMF in a 200 ml three-necked flask. Then, the resulting solution was cooled to −15° C. and to this, 1.08 g (27 mmol) of a 60% solution of NaH was added over 0.5 hours. After addition, the mixed solution was stirred at −15° C. for 1 hour. Then, 3.00 g (13.5 mmol) of 9,10-bis(chloromethyl)anthracene (1) was added gradually in a crystalline state. The resulting mixture was heated to −10° C. after a lapse of one hour from the completion of this addition and stirred over one night. After the completion of a reaction, DMF was distilled off under a reduced pressure, and the residue was dissolved in 200 ml of methylene chloride and insoluble matter was filtered out. 50 ml of water was added to this, and TFA was added while stirring until the pH of the solution becomes acid. After leaving at rest for 15 minutes, the solution was separated into two layers. A water phase was concentrated by repeating this operation two times and then the water phase was freeze-dried to obtain 2.43 g of quaternary anthracene salt 2 at a yield of 33%.

Source