Adamantanylideneadamantane [30541-56-1]
|
 |
| |
|---|
| Name | Adamantanylideneadamantane |
| Synonyms |
|
| Name in Chemical Abstracts | Tricyclo[3.3.1.1(3,7)]decane, tricyclo[3.3.1.1(3,7)]decylidene- |
| CAS No | 30541-56-1 |
| EINECS No |
|
| Molecular formula | C20H28 |
| Molecular mass | 268.45 |
| SMILES code | C1(=C6C4CC5CC(C4)CC6C5)C2CC3CC(C2)CC1C3 |
|
| TiCl4 / Zn / THF |
 |
|
|
|
; Side reactions |
1H-NMR
| 1H-NMR: crude product |
| 500 MHz, CDCl3 |
| delta [ppm] | mult. | atoms | assignment |
| 1.63-1.69 | m | 8 H | CH2 |
| 1.79-1.86 | m | 12 H | CH2 |
| 1.90 | m | 4 H | 5-H, 5'-H, 7-H, 7'-H |
| 2.88 | m | 4 H | 1-H, 1'-H, 3-H, 3'-H |
| 7.26 |
|
| CHCl3 |
|
|
|
|
| 1H-NMR: Adamantanylideneadamantane |
| 500 MHz, CDCl3 |
| delta [ppm] | mult. | atoms | assignment |
| 1.63-1.69 | m | 8 H | CH2 |
| 1.79-1.86 | m | 12 H | CH2 |
| 1.90 | m | 4 H | 5-H, 5'-H, 7-H, 7'-H |
| 2.88 | m | 4 H | 1-H, 1'-H, 3-H, 3'-H |
| 7.26 |
|
| CHCl3 |
|
|
|
|
Synthesis of adamantylideneadamantane from adamantanone
| Reaction type: |
McMurry reaction, reductive coupling, alkenesynthesis |
| Substance classes: |
ketone, alkene |
| Techniques: |
working with cover gas, adding dropwise with a piston-operated
pipette, adding dropwise with an addition funnel, stirring with magnetic
stir bar, heating under reflux, shaking out, extracting, Abfiltrieren,
evaporating with rotary evaporator, recrystallizing, use of an ice
cooling bath, heating with oil bath |
| Degree of difficulty: |
Difficult |
http://kriemhild.uft.uni-bremen.de/nop/en/instructions/pdf/3012_en.pdf
Operating scheme
| Educts |
|
Amount |
Risk |
Safety |
| 2-Adamantanone |
|
15.0 g |
R no data
|
S 24/25
|
| Reagents |
|
Amount |
Risk |
Safety |
| Titanium tetrachloride |
 |
C |
|
20.3 g |
R 14-34
|
S 1/2-7/8-26-36/37/39-45
|
| Zinc powder |
 |
F |
 |
N |
|
14.3 g |
R 15-17-50/53
|
S 2-43-46-60-61
|
| Solvents |
|
Amount |
Risk |
Safety |
| Tetrahydrofuran |
|
F |
 |
Xi |
|
430 mL |
R 11-19-36/37
|
S 2-16-29-33
|
| Cyclohexane |
|
~250 mL |
R 11-38-50/53-65-67
|
S 2-9-16-33-60-61-62
|
| Ethanol |
|
F |
|
|
R 11
|
S 2-7-16
|
| Others |
|
Amount |
Risk |
Safety |
| Potassium carbonate |
 |
Xn |
|
~21 g |
R 22-36/37/38
|
S 22-26-37/39
|
| Sodium sulfate |
|
Xi |
|
~5 g |
R 36/37/38
|
S 26-36 |
| Products |
|
Amount |
Risk |
Safety |
| Adamantanylideneadamantane |
|
11.4 g |
R no data
|
S no data
|
| Byproducts |
|
Amount |
Risk |
Safety |
| 2-Adamantanol |
|
|
R no data
|
S 24/25
|
| Waste |
Disposal |
|---|
| evaporated solvent mixture
|
organic solvents, halogen free
|
| aqueous phase after shaking out
|
solvent water mixtures, containing halogens
|
| sodium sulfate
|
solid waste, free from mercury
|
|
three-necked flask 1000 mL |
|
|
heatable magnetic stirrer with magnetic stir bar |
|
internal thermometer |
|
|
suction filter |
|
suction flask |
|
|
bubble counter |
|
piston-operated pipette |
|
|
protective gas piping |
|
addition funnel with pressure balance |
|
|
separating funnel |
|
rotary evaporator |
|
|
ice bath |
|
oil bath |
|
|
| Atom economy |
|
48.3 |
% |
| Yield |
|
85 |
% |
| Target product mass |
|
11.4 |
g |
| Sum of input masses |
|
430 |
g |
| Mass efficiency |
|
26 |
mg/g |
| Mass index |
|
38 |
g input / g product |
| E factor |
|
37 |
g waste / g product |
Chromatogram
| GC: crude product |
| column | SE-54, L= 25 m, ID 0.32 mm, DF 0.25 µm (Macherey & Nagel) |
| inlet | Gerstel KAS, injector: 250°C, split injection 1:20, 0.1 µL |
| carrier gas | N2, pre-column pressure 62 kPa, 1.04 mL/min |
| oven | 100 °C (1 min), 10 °C/min --> 250 °C (30 min) |
| detector | FID, 275 °C |
| integration | percent concentration calculated from relative peak area |
| GC: pure product |
| column | SE-54, L= 25 m, ID 0.32 mm, DF 0.25 µm (Macherey & Nagel) |
| inlet | Gerstel KAS, injector: 250°C, split injection 1:20, 0.1 µL |
| carrier gas | N2, pre-column pressure 62 kPa, 1.04 mL/min |
| oven | 100 °C (1 min), 10 °C/min --> 250 °C (30 min) |
| detector | FID, 275 °C |
| integration | percent concentration calculated from relative peak area |
13C-NMR
| 13C-NMR: crude product |
| 125 MHz, CDCl3 |
| delta [ppm] | assignment |
| 28.6 | C5, C5', C7, C7' |
| 31.9 | C1, C1', C-3, C3' |
| 37.3 | C6, C6' |
| 39.6 | C4, C4', C8, C8', C9, C9', C10, C10' |
| 133.1 | C2, C2' |
| 76.5-77.5 | CDCl3 |
|
|
| 13C-NMR: Adamantanylideneadamantane |
| 125 MHz, CDCl3 |
| delta [ppm] | assignment |
| 28.6 | C5, C5', C7, C7' |
| 31.9 | C1, C1', C-3, C3' |
| 37.3 | C6, C6' |
| 39.6 | C4, C4', C8, C8', C9, C9', C10, C10' |
| 133.1 | C2, C2' |
| 76.5-77.5 | CDCl3 |
IR
| IR: crude product |
| [KBr, T%, cm-1] |
| [cm-1] | assignment |
| 2966, 2916 | aliph. C-H valence |
| 2848 | aliph. C-H valence |
|
|
| IR: Adamantanylideneadamantane |
| [KBr, T%, cm-1] |
| [cm-1] | assignment |
| 2966, 2916 | aliph. C-H valence |
| 2848 | aliph. C-H valence |
|
|
सुकून उतना ही देना प्रभू, जितने से जिंदगी चल जाये। औकात बस इतनी देना, कि औरों का भला हो जाये।
DRUG APPROVALS BY DR ANTHONY MELVIN CRASTO …..FOR BLOG HOME CLICK HERE
Join me on Linkedin
Join me on Facebook
FACEBOOK
Join me on twitter
amcrasto@gmail.com
LIONEL MY SON
He was only in first standard in school when I was hit by a deadly one in a million spine stroke called acute transverse mylitis, it made me 90% paralysed and bound to a wheel chair, Now I keep him as my source of inspiration and helping millions, thanks to millions of my readers who keep me going and help me to keep my son happy
सुकून उतना ही देना प्रभू, जितने से
जिंदगी चल जाये।
औकात बस इतनी देना,
कि औरों का भला हो जाये।
Take a tour
RWANDA, AFRICA
https://en.wikipedia.org/wiki/Rwanda
Rwanda (/ruːˈɑːndə/ or /ruːˈændə/), officially the Republic of Rwanda (Kinyarwanda: Repubulika y'u Rwanda; French: République du Rwanda), is a ...
https://en.wikipedia.org/wiki/Rwanda
Rwanda (/ruːˈɑːndə/ or /ruːˈændə/), officially the Republic of Rwanda (Kinyarwanda: Repubulika y'u Rwanda; French: République du Rwanda), is a ...
KIGALI
KIGALI
//////
Googleplus
