Sulfuric Acid → 4-Hydroxy-3-methyl-2-pentyl-cyclopent-2-enone

HRID 365169Notes

Reaction equation

HRID 365169 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.S(=O)(=O)(O)[OH:18]>O1CCCC1>[OH:18][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]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 135172551-Methyl-4-oxo-5-pentylcyclopent-2-en-1-yl acetate

Product 1

HCID 122257564-Hydroxy-3-methyl-2-pentyl-cyclopent-2-enone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In the same flask as in Example 1, there were charged 3-acetoxy-2-n-pentyl-3-methyl-4-cyclopentenone (2.24 g), tetrahydrofuran (10 ml) and 20% sulfuric acid (10 ml), and the resultant mixture was stirred at 30° to 50° C. for 6 hours. After completion of the reaction, the reaction mixture was subjected to post-treatment and purification as in example 1 to give 1.55 g of 4-hydroxy-2-n-pentyl-3-methyl-2-cyclopentenone. Yield, 85%.

Workup

  1. customAfter completion of the reaction
  2. custompurification as in example 1

Sources & evidence

ORD record
ord-e3c22cd44e024245bfdac5e1d30226cb
Source dataset
uspto-grants-1986_08
Patent number
US04608442

Reaction notes

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