Sulfuric Acid → 2-Hydroxybicyclo(2.2.1)heptane-2-carboxylic acid

HRID 258443

반응식

HRID 258443 반응식
[OH-].[K+].[Mn]([O-])(=O)(=O)=O.[K+].[CH:9]12[CH2:15][CH:12]([CH2:13][CH2:14]1)[CH2:11][CH:10]2[C:16]([OH:18])=[O:17].S(=O)(=O)(O)[OH:20].S(=O)(O)[O-].[Na+]>O>[OH:20][C:10]1([C:16]([OH:18])=[O:17])[CH2:11][CH:12]2[CH2:15][CH:9]1[CH2:14][CH2:13]2

참가 물질

7

반응물 5

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 79113Bicyclo[2.2.1]heptane-2-carboxylic acidHCID 516875Potassium PermanganateHCID 23665763Sodium Bisulfite

생성물 1

HCID 123869462-Hydroxybicyclo(2.2.1)heptane-2-carboxylic acid

시약·촉매·용매 1

HCID 962Water용매

실험 절차

24.1 g (367 mmol) of potassium hydroxide (85%) and 18.9 g (120 mmol) of potassium permanganate were dissolved in 84 ml of water, on ice cooling, 8.36 g (59.6 mmol) of crude 2-norbornane carboxylic acid in 84 ml of petroleum ether was added dropwise. After heating and refluxing for six hours, the mixture was stirred at room temperature for 18 hours. On ice cooling, the reaction mixture was slowly added into 120 ml of 6N sulfuric acid, 60 ml of an aqueous solution of 13.0 g of sodium bisulfite was added to the acid mixture, and the solution was stirred at room temperature for one hour. The solution was extracted with ether (100 ml×4), and the extract was dried over anhydrous magnesium sulfate and filtered. The solvent was distilled off, and 8.34 g of crude 2-hydroxy-2-norbornanecarboxylic acid was obtained. Crude yield: 90%.

후처리

  1. additionwas added dropwise
  2. temperatureAfter heating
  3. temperaturerefluxing for six hours
  4. additionwas added to the acid mixture
  5. stirringthe solution was stirred at room temperature for one hour
  6. extractionThe solution was extracted with ether (100 ml×4)
  7. dry with materialthe extract was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. distillationThe solvent was distilled off

출처 및 근거

ORD 기록
ord-437646fd0a764c8499b106a0003bbaa0
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05266728

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