Sulfuric Acid → 10-Cycloeicosenone

HRID 1883286

Reaction equation

HRID 1883286 reaction equation
[OH:1][CH:2]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=[CH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.C1(C)C=CC=CC=1.S(=O)(=O)(O)O>[Zn].O>[C:2]1(=[O:1])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=[CH:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 1140Toluene2×HCID 673128522-Hydroxy-11-cycloeicosenone

Product 1

HCID 6731346910-CycloeicosenoneYield 92%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

In a 50 ml four neck reactor equipped with a thermometer, a dripping funnel and a refrigerant, zinc powder (2.3 g), 2-hydroxy-11-cycloeicosenone (1.4 g) and toluene (10 ml) were mixed, stirred and heated at 90° C. under nitrogen flow. A 20N sulphuric acid aqueous-solution (2.8 ml) was added thereto dropwise over 2.5 hours and the resulting mixture was stirred under heating for 30 minutes. Toluene and water were added after the reaction and the resulting solution was allowed to stand to separate into two phases. The organic phase was washed twice with water and then washed with a saturated sodium chloride aqueous solution. The solvent was removed under reduced pressure to give 1.4 g of crude product. The crude product was purified on a silica gel column chromatograph (hexane/ethyl acetate=10/1, v/v) to give 1.2 g of 10-cycloeicosenone (yield 92%).

Workup

  1. stirringthe resulting mixture was stirred
  2. temperatureunder heating for 30 minutes
  3. customafter the reaction
  4. customto separate into two phases
  5. washThe organic phase was washed twice with water
  6. washwashed with a saturated sodium chloride aqueous solution
  7. customThe solvent was removed under reduced pressure
  8. customto give 1.4 g of crude product
  9. customThe crude product was purified on a silica gel column chromatograph (hexane/ethyl acetate=10/1

Sources & evidence

ORD record
ord-13f9e2294eca4c6db11810efce91b7e2
Source dataset
uspto-grants-2004_07
Patent number
US06759557B2

Linked notes

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