Water → HCID 567350, compound

HRID 2370299Notes

Reaction equation

HRID 2370299 reaction equation
[CH:1]12[CH2:10][CH:5]([C:6](=[O:9])[CH2:7][CH2:8]1)[CH2:4][CH2:3][C:2]2=[O:11].[C:12]1([CH3:22])C(S(O)(=O)=O)=CC=CC=1.[OH2:23]>C(O)CO>[CH2:12]1[O:23][C:2]2([CH2:3][CH2:4][CH:5]3[CH2:10][CH:1]2[CH2:8][CH2:7][C:6]3=[O:9])[O:11][CH2:22]1

Participants

5

Reactant 3

HCID 962WaterHCID 69252-Methylbenzenesulfonic acidHCID 140084Bicyclo[3.3.1]nonane-2,6-dione

Product 1

HCID 567350HCID 567350, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

5 g of bicyclo[3.3.1]nonane-2,6-dione were suspended in 27 mL of dry ethylene glycol and 283 mg of p toluene sulfonic acid were added. After 2 h all starting material was converted. 80 mL of water were added and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and sat. sodium bicarbonate, dried over sodium sulfate and evaporated to dryness. The crude product was purified by silica gel chromatography to give 0.5 g of the desired product along with 6.75 g of the diketal. The diketal was dissolved in 135 mL of acetone and 13.5 mL of 2M HCl were added. The mixture was allowed to stir at room temperature for 1 h. The mixture was neutralized by addition of 2 N NaOH, the acetone was removed in vacuo and the remaining aqueous layer was extracted with ethyl acetate and dichloromethane. The organic layer was dried over sodium sulfate and evaporated to dryness. The crude product was purified by chromatography to give another 4.38 g of the desired product. Rt=0.84 min (Method C). Detected mass: 197.2 (M+H+).

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe combined organic layer was washed with water and sat. sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a0f42c2814054f7885729af6db300123
Source dataset
uspto-grants-2014_04
Patent number
US08710077B2

Reaction notes

Loading…