franklyloveyou
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2,2-dinotropropanol synthesis
Hey All
I'm looking for tips on 2,2-dinotropropanol synthesis. Is here someone who has info about 2,2-dinotropropanol synthesis?
thanks in advanced
[Edited on 19-2-2016 by franklyloveyou]
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hissingnoise
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| Quote: | | Is here someone who has info about 2,2-dinotropropanol synthesis? |
No one here has ever even heard of this compound ─ and BTW, your moniker would suggest you've already been 'imbibing' your target product . . . ?
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Bert
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Thread Moved
19-2-2016 at 06:44 |
Waffles SS
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Quote: Originally posted by franklyloveyou  | Hey All
I'm looking for tips on 2,2-dinotropropanol synthesis. Is here someone who has info about 2,2-dinotropropanol synthesis?
thanks in advanced
[Edited on 19-2-2016 by franklyloveyou] |
| Quote: |
2,2-Dinitropropanol
To a stirred solution of 2.66 g (66.5 mmoles) of sodium hydroxide in 15 ml of water at 20° was added 5.0 g (66.5 mmoles) of nitroethane.When all the
nitroethane dissolved, the solution was cooled to 5°-7° in an ice-water bath and 5.4 g of 37percent aqueous formaldehyde (66.5 mmoles) was then
added.The cooling bath was removed and the mixture was stirred for 2 hours before the ice-water bath was replaced and 25 ml of ether was added.A
solution of 18.3 g of sodium nitrite (0.265 mole) in 30 ml of water was then added followed by solutions of 15.8 g (66.3 mmoles) of sodium persulfate
in 30 ml of water and 4.4 g (13.4 mmoles) of potassium ferricyanide in 15 ml of water.The reaction temperature rose from 14° to 35°.The mixture was
then stirred at ambient temperature for 1 hour and phases were separated.The aqueous phase was extracted twice with ether and the combined ether
extracts were washed with brine and dried.The product was distilled in a short path distillation apparatus to give 6.57 g (65percent yield) of
2,2-dinitropropanol.
US4594430
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| Quote: |
2,2-Dinitropropanol
A homogeneous solution, prepared from 2.75 g (68 mmol) of sodium hydroxide, 5.00 g (67 mmol) of nitroethane,and 20 mL of water, was stirred with 5.50
g (68 mmol)of 37% formalin for 2 h. Tetrahydrofuran (50 mL) and a solution of 18 g (0.26 mol) of sodium nitrite in 40 mL of water were added,and the
mixture was cooled to 15 "C. A solution of 4.4 g (13 mmol)of potassium ferricyanide in 15 mL of water and a solution of 16 g (67 mmol) of sodium
persulfate in 30 mL of water were added with ice bath cooling. The mixture was stirred for 1 h at 20 "C and was then extracted three times with ether.
The combined organic layers were washed with brine and dried over magnesium sulfate. Distillation gave 0.40 g of a forerun, bp <80 "C (0.1 mm),
consisting of 50% 2,2-dinitropropanol and 50% 1,l-dinitroethane,and 6.7 g (67%) of 2,2 dinitropropanol: bp 90-100 "C (0.1 mm);mp2,9 79-80 "C; NMR
(CDC13) 6 2.15 (s, 3 H), 3.40, (br s, 1 H,DzO exch), 4.30 (s, 2 H).
Garver, Lee C.; Grakauskas, V.; Baum, Kurt
Journal of Organic Chemistry, 1985 , vol. 50, # 10 p. 1699 - 1702
DOI:10.1021/jo00210a600
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[Edited on 19-2-2016 by Waffles SS]
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franklyloveyou
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Yeap; It's kind of alcohol
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franklyloveyou
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| Quote: Originally posted by Waffles SS | | Quote: Originally posted by franklyloveyou | Hey All
I'm looking for tips on 2,2-dinotropropanol synthesis. Is here someone who has info about 2,2-dinotropropanol synthesis?
thanks in advanced
[Edited on 19-2-2016 by franklyloveyou] |
| Quote: |
2,2-Dinitropropanol
To a stirred solution of 2.66 g (66.5 mmoles) of sodium hydroxide in 15 ml of water at 20° was added 5.0 g (66.5 mmoles) of nitroethane.When all the
nitroethane dissolved, the solution was cooled to 5°-7° in an ice-water bath and 5.4 g of 37percent aqueous formaldehyde (66.5 mmoles) was then
added.The cooling bath was removed and the mixture was stirred for 2 hours before the ice-water bath was replaced and 25 ml of ether was added.A
solution of 18.3 g of sodium nitrite (0.265 mole) in 30 ml of water was then added followed by solutions of 15.8 g (66.3 mmoles) of sodium persulfate
in 30 ml of water and 4.4 g (13.4 mmoles) of potassium ferricyanide in 15 ml of water.The reaction temperature rose from 14° to 35°.The mixture was
then stirred at ambient temperature for 1 hour and phases were separated.The aqueous phase was extracted twice with ether and the combined ether
extracts were washed with brine and dried.The product was distilled in a short path distillation apparatus to give 6.57 g (65percent yield) of
2,2-dinitropropanol.
US4594430
|
| Quote: |
2,2-Dinitropropanol
A homogeneous solution, prepared from 2.75 g (68 mmol) of sodium hydroxide, 5.00 g (67 mmol) of nitroethane,and 20 mL of water, was stirred with 5.50
g (68 mmol)of 37% formalin for 2 h. Tetrahydrofuran (50 mL) and a solution of 18 g (0.26 mol) of sodium nitrite in 40 mL of water were added,and the
mixture was cooled to 15 "C. A solution of 4.4 g (13 mmol)of potassium ferricyanide in 15 mL of water and a solution of 16 g (67 mmol) of sodium
persulfate in 30 mL of water were added with ice bath cooling. The mixture was stirred for 1 h at 20 "C and was then extracted three times with ether.
The combined organic layers were washed with brine and dried over magnesium sulfate. Distillation gave 0.40 g of a forerun, bp <80 "C (0.1 mm),
consisting of 50% 2,2-dinitropropanol and 50% 1,l-dinitroethane,and 6.7 g (67%) of 2,2 dinitropropanol: bp 90-100 "C (0.1 mm);mp2,9 79-80 "C; NMR
(CDC13) 6 2.15 (s, 3 H), 3.40, (br s, 1 H,DzO exch), 4.30 (s, 2 H).
Garver, Lee C.; Grakauskas, V.; Baum, Kurt
Journal of Organic Chemistry, 1985 , vol. 50, # 10 p. 1699 - 1702
DOI:10.1021/jo00210a600
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[Edited on 19-2-2016 by Waffles SS] |
Really thanks Waffles SS
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