Acetic Acid → 2-Cyclopenten-1-one, 2-methoxy-3-methyl-

HRID 851350Notes

Reaction equation

HRID 851350 reaction equation
COC.[O:4]1[CH2:9][CH2:8][O:7][CH2:6]C1.C(N([CH2:15][CH3:16])CC)C.[C:17](O)(=O)[CH3:18]>>[CH3:6][O:7][C:8]1[C:9](=[O:4])[CH2:17][CH2:18][C:15]=1[CH3:16]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 8254Dimethyl EtherHCID 8471TriethylamineHCID 312751,4-Dioxane

Product 1

HCID 842492-Cyclopenten-1-one, 2-methoxy-3-methyl-

Conditions

Temperature
100 °C

Procedure

A 3.06 g quantity (0.0212 mol) of methyl ether of 2,5-diketohexanol-1 is added to 15 ml of dioxane containing 5% of triethylamine, and the mixture is heated at 100° C. for 2 hours. The reaction product is carefully neutralized with acetic acid and thereafter distilled at reduced pressure, giving 2-methoxy-3-methyl-cyclopentenone, the desired product, in a yield of 88%, b.p. 84°-85° C./18 mm Hg.

Workup

  1. distillationdistilled at reduced pressure

Sources & evidence

ORD record
ord-7df12435ac7c4f77a6b37caa9bc99f7a
Source dataset
uspto-grants-1983_05
Patent number
US04384144

Reaction notes

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