Calcium Carbonate → 2-(1-Phenylcyclopentyl)acetaldehyde

HRID 977865Notes

Reaction equation

HRID 977865 reaction equation
[C:1](=[O:4])([O-])[O-].[Ca+2].[C:6]1([C:12]2([CH2:17]C3SCCCS3)[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(#N)C.O.C(OCC)(=O)C>[C:6]1([C:12]2([CH2:17][CH:1]=[O:4])[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 2

HCID 10112Calcium CarbonateHCID 199661182-(1-Phenylcyclopentyl)methyl-1,3-dithiane

Product 1

HCID 199660432-(1-Phenylcyclopentyl)acetaldehydeYield 96%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

263 mg (0.969 mmol) of mercuric chloride and 129 mg (1.29 mmol) of calcium carbonate were added to a suspension of 90 mg (0.323 mmol) of 2-(1-phenylcyclopentyl)methyl-1,3-dithiane [prepared as described in step (iv) above] in a mixture of 4 ml of acetonitrile and 0.6 ml of water, and the resulting mixture was stirred for 3 hours at 90° C. At the end of this time, the reaction mixture was cooled and then diluted with ethyl acetate. The insoluble materials were filtered off from the diluted mixture with the help of Celite (trade mark) filter aid. The filtrate was then washed with a 1M aqueous solution of sodium acetate, with a saturated aqueous solution of ammonium chloride and with a saturated aqueous solution of sodium chloride, in that order. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through 5 g of silica gel, using methylene chloride as the eluent, to give 58.4 mg (yield 96%) of the title compound as a foam-like material.

Workup

  1. temperatureAt the end of this time, the reaction mixture was cooled
  2. filtrationThe insoluble materials were filtered off from the diluted mixture with the help of Celite (trade mark)
  3. filtrationfilter aid
  4. washThe filtrate was then washed with a 1M aqueous solution of sodium acetate, with a saturated aqueous solution of ammonium chloride and with a saturated aqueous solution of sodium chloride, in that order
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe resulting residue was purified by column chromatography through 5 g of silica gel

Sources & evidence

ORD record
ord-d62f1122f4cc4a32b4c97e6b4bb6eb9c
Source dataset
uspto-grants-1997_03
Patent number
US05614550

Reaction notes

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