Water → 5-(5-Oxocyclopent-1-en-1-yl)pentyl acetate

HRID 1439092Notes

Reaction equation

HRID 1439092 reaction equation
C(=O)([O-])[O-].[Ca+2].O.C([O:10][C:11]1[CH2:15][CH2:14][CH2:13][C:12]=1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22](=[O:24])[CH3:23])(=O)C.BrBr>CN(C)C(=O)C.C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[C:22]([O:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][C:12]1[C:11](=[O:10])[CH2:15][CH2:14][CH:13]=1)(=[O:24])[CH3:23]

Participants

8

Reactant 4

HCID 962WaterHCID 10112Calcium Carbonate2×HCID 24408BromineHCID 20465612HCID 20465612, compound

Product 1

HCID 132897885-(5-Oxocyclopent-1-en-1-yl)pentyl acetate

Reagents, catalysts & solvents 3

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolventHCID 31374DimethylacetamideSolvent

Procedure

To a well stirred mixture of 405 g. (4.05 moles) of calcium carbonate, 3 l. of water, and 2.5 l. of chloroform cooled to 5° C. is added simultaneously 1016 g. (4.0 moles) of 1-acetoxy-2-(5-acetoxy-pentyl)-1-cyclopentene (Example 56) and a solution of 648 g. (4.05 moles) of bromine in 500 ml. of carbon tetrachloride at a rate to maintain a temperature below 10° C. The mixture is stirred for half an hour after addition of the reagents and the phases are then separated. The organic phase is washed with 2% sodium thiosulfate solution, water, and saturated brine, dried (MgSO4), and evaporated in vacuo to an oil. The oil is immediately added to a refluxing slurry of 500 g. (5.0 moles) of calcium carbonate in 2.5 l. of N,N-dimethylacetamide under nitrogen and the mixture is then refluxed for 30 minutes. The mixture is cooled, filtered, and partitioned between water and diethyl ether. The organic phase is washed with water and saturated brine, dried (MgSO4), and evaporated to yield 757 g. of an oil, b.p. 116°-118° C. (0.25 mm.).

Workup

  1. additionmixture of 405 g
  2. additionis added simultaneously 1016 g
  3. stirringThe mixture is stirred for half an hour
  4. additionafter addition of the reagents
  5. customthe phases are then separated
  6. washThe organic phase is washed with 2% sodium thiosulfate solution, water, and saturated brine
  7. dry with materialdried (MgSO4)
  8. customevaporated in vacuo to an oil
  9. additionThe oil is immediately added to a refluxing slurry of 500 g
  10. temperatureThe mixture is cooled
  11. filtrationfiltered
  12. custompartitioned between water and diethyl ether
  13. washThe organic phase is washed with water and saturated brine
  14. dry with materialdried (MgSO4)
  15. customevaporated
  16. customto yield 757 g

Sources & evidence

ORD record
ord-1c1a840641d6437190f8c939a23a648d
Source dataset
uspto-grants-1977_11
Patent number
USRE029469

Reaction notes

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