Formaldehyde → 2,2-Dinitropropanol

HRID 1165575

반응식

HRID 1165575 반응식
[OH-:1].[Na+].[N+:3]([CH2:6][CH3:7])([O-:5])=[O:4].[CH2:8]=O.[N:10]([O-:12])=[O:11].[Na+].S(OOS([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+]>O.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[N+:3]([C:6]([N+:10]([O-:12])=[O:11])([CH3:8])[CH2:7][OH:1])([O-:5])=[O:4]

참가 물질

8

반응물 5

HCID 712FormaldehydeHCID 6587Nitroethane2회HCID 14798Sodium HydroxideHCID 62655Sodium PersulfateHCID 23668193Sodium Nitrite

생성물 1

HCID 701942,2-Dinitropropanol수율 65.8%

시약·촉매·용매 2

HCID 178511488HCID 178511488, 화합물촉매HCID 962Water용매4회

실험 절차

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 37% 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 (65% yield) of 2,2-dinitropropanol.

후처리

  1. temperaturethe solution was cooled to 5°-7° in an ice-water bath
  2. customThe cooling bath was removed
  3. addition25 ml of ether was added
  4. customrose from 14° to 35°
  5. stirringThe mixture was then stirred at ambient temperature for 1 hour
  6. customphases were separated
  7. extractionThe aqueous phase was extracted twice with ether
  8. washthe combined ether extracts were washed with brine
  9. customdried
  10. distillationThe product was distilled in a short path distillation apparatus

출처 및 근거

ORD 기록
ord-667b82bae5b2427fbeb5a1d2390d17c7
출처 데이터셋
uspto-grants-1990_03
특허 번호
US04910322

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