Ethanol → Ethyl 9-(5-oxocyclopent-1-en-1-yl)nonanoate

HRID 839320Notes

Reaction equation

HRID 839320 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[C:13](=[O:17])[CH2:14][CH2:15][CH:16]=1)([OH:3])=[O:2].[CH2:18](O)[CH3:19].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[C:13](=[O:17])[CH2:14][CH2:15][CH:16]=1)([O:3][CH2:18][CH3:19])=[O:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 21767809HCID 21767809, compound

Product 1

HCID 13046302Ethyl 9-(5-oxocyclopent-1-en-1-yl)nonanoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The acid ketone from Example 22 is Fisher esterified with 100 ml. of absolute ethanol, 100 ml. of benzene, and 20 mg. of p-toluenesulfonic acid for 6 hours, cooled, and the solvent is evaporated. The resulting oil is dissolved in 3:1 benzene-ether and the solution is passed through a column of 100 g. of Florisil® . The filtrate is evaporated and the residue is distilled to yield 2.97 g. of a colorless oil, b.p. 137°-139° C. (0.05 Torr).

Workup

  1. temperaturecooled
  2. customthe solvent is evaporated
  3. dissolutionThe resulting oil is dissolved in 3:1 benzene-ether
  4. customThe filtrate is evaporated
  5. distillationthe residue is distilled
  6. customto yield 2.97 g

Sources & evidence

ORD record
ord-4751772d620d48329a00b943c2cb3382
Source dataset
uspto-grants-1978_06
Patent number
US04094896

Reaction notes

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