Sulfuric Acid → 1-Acetoxy-2-(6-carbomethoxyhexyl)-cyclopent-1-ene

HRID 2071355Notes

Reaction equation

HRID 2071355 reaction equation
[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[O:16])([O:3][CH3:4])=[O:2].[C:17](OC(C)=C)(=[O:19])[CH3:18].S(=O)(=O)(O)O>>[C:17]([O:16][C:12]1[CH2:13][CH2:14][CH2:15][C:11]=1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:1]([O:3][CH3:4])=[O:2])(=[O:19])[CH3:18]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7916Isopropenyl acetateHCID 13099223Methyl 7-(2-oxocyclopentyl)heptanoate

Product 1

HCID 214135791-Acetoxy-2-(6-carbomethoxyhexyl)-cyclopent-1-ene

Procedure

This preparation illustrates methods for preparing 1-acyloxy-2-(carboalkoxy-alkyl)-cyclopent-1-ene. In this example, 26.5 g. of 2-(6-carbomethoxy-hexyl)-1-oxo-cyclopentane is added to 250 ml. of isopropenyl acetate containing 0.4 ml. of concentrated sulfuric acid. The mixture is then slowly distilled for 21/2 hours and then cooled to room temperature and poured into an ice saturated solution of aqueous sodium bicarbonate. The mixture is then extracted with methylene chloride. The methylene chloride extract is washed with water and then washed with saturated brine, then dried over anhydrous sodium sulfate and evaporated to dryness affording a crude residue of 1-acetoxy-2-(6-carbomethoxyhexyl)-cyclopent-1-ene, which is further purified by high vacuum distillation.

Workup

  1. distillationThe mixture is then slowly distilled for 21/2 hours
  2. additionpoured into an ice saturated solution of aqueous sodium bicarbonate
  3. extractionThe mixture is then extracted with methylene chloride
  4. extractionThe methylene chloride extract
  5. washis washed with water
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-023b3d47b51146ff92d5db49d406fc0f
Source dataset
uspto-grants-1977_09
Patent number
US04046801

Reaction notes

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