Toluene → HCID 13335396, compound

HRID 485122Notes

Reaction equation

HRID 485122 reaction equation
C(O[C:5]1([CH3:16])[CH:9]=[CH:8][C:7](=[O:10])[CH:6]1[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])(=O)C.C1(C)C=CC=CC=1.[C:24]([O-:27])(=[O:26])[CH3:25].[Na+]>C(O)(=O)C>[C:24]([O:27][CH:9]1[CH2:8][C:7](=[O:10])[C:6]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[C:5]1[CH3:16])(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 1140TolueneHCID 517045Sodium AcetateHCID 135172551-Methyl-4-oxo-5-pentylcyclopent-2-en-1-yl acetate

Product 1

HCID 13335396HCID 13335396, compoundYield 170.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

In the same apparatus as in Example 1, 3-acetoxy-2-n-pentyl-3-methyl-4-cyclopentenone (22.4 g), toluene (60 ml), acetic acid (10 ml) and sodium acetate (4 g) were charged and heated for 10 hours with agitation. After the completion of the reaction, acetic acid was evaporated off under reduced pressure. The residue was extracted with toluene (70 ml) and water (50 ml) and treated as in Example 1 to obtain 4-acetoxy-2-n-pentyl-3-methyl-2-cyclopentenone (18.6 g). Yield, 83%, B.P., 125°-135° C./0.2-0.5 mmHg.

Workup

  1. temperatureheated for 10 hours with agitation
  2. customwas evaporated off under reduced pressure
  3. extractionThe residue was extracted with toluene (70 ml) and water (50 ml)
  4. additiontreated as in Example 1

Sources & evidence

ORD record
ord-6dbcf61aa4db493194f3564955be7f59
Source dataset
uspto-grants-1985_08
Patent number
US04535182

Reaction notes

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