反応 #576138

反応方程式

3,10-dihexyl-7,14-dihydropentacene-5,12-dione

→

2,9-dihexylpentacene

溶媒

2-methoxyethyl ether

反応条件

後処理

1. 1
   その他flushed with nitrogen for 15 minutes
2. 2
   workup.ADDITIONTo this was added 13.4 grams of sodium borohydride
3. 3
   workup.STIRRINGstirring
4. 4
   workup.ADDITIONTo the resulting mixture was added 126 mL of methanol over 1.25 hours
5. 5
   温度was maintained at 40° C. during the addition by intermittent application of a cold water bath
6. 6
   workup.ADDITIONWhen addition
7. 7
   workup.STIRRINGwas complete stirring
8. 8
   その他was continued at room temperature
9. 9
   workup.STIRRINGAfter stirring for 2 hours at room temperature an additional 50 mL of 2-methoxyethyl ether
10. 10
    workup.ADDITIONwas added
11. 11
    workup.STIRRINGAfter stirring with methanol for a total of 3.5 hours, 300 mL of acetic acid
12. 12
    workup.ADDITIONwas added
13. 13
    温度the resulting mixture was heated to 60° C. for 1.5 hours
14. 14
    workup.ADDITIONTo the mixture was added 100 mL of concentrated hydrochloric acid
15. 15
    温度heating at 60° C.
16. 16
    workup.WAITwas continued for one hour
17. 17
    温度The mixture was cooled to room temperature
18. 18
    ろ過the resulting solid was collected by filtration
19. 19
    洗浄washed with 500 mL of water
20. 20
    洗浄The solid was washed with 500 mL of acetone
21. 21
    洗浄The solid was washed with an additional one liter of acetone
22. 22
    その他dried

実験手順

A mixture of 20 grams of 3,10-dihexyl-7,14-dihydropentacene-5,12-dione and 200 mL of 2-methoxyethyl ether was stirred and flushed with nitrogen for 15 minutes. To this was added 13.4 grams of sodium borohydride, and stirring was continued at room temperature overnight. To the resulting mixture was added 126 mL of methanol over 1.25 hours. The temperature increased to 40° C. and was maintained at 40° C. during the addition by intermittent application of a cold water bath. When addition was complete stirring was continued at room temperature. After stirring for 2 hours at room temperature an additional 50 mL of 2-methoxyethyl ether was added. After stirring with methanol for a total of 3.5 hours, 300 mL of acetic acid was added, and the resulting mixture was heated to 60° C. for 1.5 hours. To the mixture was added 100 mL of concentrated hydrochloric acid and heating at 60° C. was continued for one hour. The mixture was cooled to room temperature and the resulting solid was collected by filtration and washed with 500 mL of water. The solid was washed with 500 mL of acetone and then 60 mL of tetrahydrofuran. The solid was washed with an additional one liter of acetone and dried to give 2,9-dihexylpentacene.

出典