Water → cis-3,5-Diacetoxy-1-cyclopentene

HRID 1414429Notes

Reaction equation

HRID 1414429 reaction equation
Br[C@H:2]1[CH2:6][C@@H:5](Br)[CH:4]=[CH:3]1.[C:8]([O-:11])(=[O:10])[CH3:9].[K+].C(Cl)(Cl)(Cl)Cl.[OH2:18].CC[O:21][CH2:22][CH3:23]>[Cl-].C([N+](C)(C)C)CCCCCCCCCCCCCCC>[C:8]([O:11][C@H:2]1[CH2:6][C@@H:5]([O:21][C:22](=[O:18])[CH3:23])[CH:4]=[CH:3]1)(=[O:10])[CH3:9]

Participants

7

Reactant 5

HCID 962WaterHCID 3283Diethyl EtherHCID 5943Carbon TetrachlorideHCID 517044Potassium AcetateHCID 10955247Cyclopentene, 3,5-dibromo-, cis-

Product 1

HCID 10192610cis-3,5-Diacetoxy-1-cyclopenteneYield 77%

Reagents, catalysts & solvents 1

HCID 8154Hexadecyltrimethylammonium chlorideCatalyst

Procedure

One (1.0) g of cis-1,4-dibromocyclopent-2-ene, 3.5 g of potassium acetate, 0.7 g of cetyltrimethylammonium chloride, 5 ml of carbon tetrachloride, and 2 ml of water were used in the manner similar to the Example 1, at 42° C. for 6 hours. After addition of 30 ml of ether, the organic phase was dried over sodium sulfate, and the organic solvent was distilled off under a reduced pressure similarly to Example 1. Further subjecting the residual system to a reduced pressure distillation, 0.7 g of cis-1,4-diacetoxycyclopent-2-ene boiling at 60°-61° C./0.03 mmHg was obtained. The yield was 77%.

Workup

  1. dry with materialthe organic phase was dried over sodium sulfate
  2. distillationthe organic solvent was distilled off under a reduced pressure similarly to Example 1
  3. distillationto a reduced pressure distillation

Sources & evidence

ORD record
ord-e6073b52a36b456499751a41d07e08a0
Source dataset
uspto-grants-1977_01
Patent number
US04001308

Reaction notes

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