Sulfuric Acid → HCID 53792494, compound

HRID 1763388Notes

Reaction equation

HRID 1763388 reaction equation
[C:1]12(O)[CH2:10][CH:6]([CH2:7][CH2:8][CH2:9]1)[CH:5]1[CH2:11][CH:2]2[CH2:3][CH2:4]1.S(=O)(=O)(O)[OH:14].[C:18](#[N:20])[CH3:19]>>[C:18]([NH:20][C:1]12[CH2:10][CH:6]([CH2:7][CH2:8][CH2:9]1)[CH:5]1[CH2:11][CH:2]2[CH2:3][CH2:4]1)(=[O:14])[CH3:19]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 13070378HCID 13070378, compound

Product 1

HCID 53792494HCID 53792494, compoundYield 98%

Procedure

10.0 Grams (60 millimoles) of tricyclo [4.3.1.12,5 ] undecane-1-ol (X=OH in formula (II)) are dissolved in 120 ml of acetonitrile. The solution is cooled and kept at 0° C, and then 25 ml of concentrated sulfuric acid are added dropwise under stirring over 45 minutes. The stirring is continued further at room temperature for 5 hours. The reaction mixture is placed onto 200 g of ice and extracted twice, each time with 100 ml of diethyl ether. The combined extracts are washed with saturated aqueous solution hydrogencarbonate solution and then with water and dried with anhydrous sodium sulfate. The solvent is distilled out and the residue is recrystallized from acetone-n-hexane to obtain 12.2 g (yield 98%) of 1-acetylaminotricyclo [4.3.1.12,5 ] undecane (I) as white crystals (m.p. 138°-139° C).

Workup

  1. temperatureThe solution is cooled
  2. customkept at 0° C
  3. waitThe stirring is continued further at room temperature for 5 hours
  4. extractionextracted twice
  5. washThe combined extracts are washed with saturated aqueous solution hydrogencarbonate solution
  6. dry with materialwith water and dried with anhydrous sodium sulfate
  7. distillationThe solvent is distilled out
  8. customthe residue is recrystallized from acetone-n-hexane

Sources & evidence

ORD record
ord-9de3ae4881624d26a7b63db4b7a28691
Source dataset
uspto-grants-1978_09
Patent number
US04111990

Reaction notes

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