Sulfuric Acid → 4-Hydroxy-3-methyl-2-(2-propynyl)-2-cyclopentene-1-one

HRID 365168

Reaction equation

HRID 365168 reaction equation
C(O[C:5]1([CH3:14])[CH:9]=[CH:8][C:7](=[O:10])[CH:6]1[CH2:11][C:12]#[CH:13])(=O)C.S(=O)(=O)(O)[OH:16]>>[OH:16][CH:9]1[CH2:8][C:7](=[O:10])[C:6]([CH2:11][C:12]#[CH:13])=[C:5]1[CH3:14]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 135172641-Methyl-4-oxo-5-(prop-2-yn-1-yl)cyclopent-2-en-1-yl acetate

Product 1

HCID 129182064-Hydroxy-3-methyl-2-(2-propynyl)-2-cyclopentene-1-one

Procedure

In the same flask as in Example 1, 20% sulfuric acid (10 ml) was charged, and dl-3-acetoxy-2-propargyl-3-methyl-4-cyclopentenone (1.92 g) was dropwise added thereto in 1 hour while keeping the inner temperature at 0° C. After completion of the dropwise addition, the resultant mixture was stirred at the same temperature as above for 3 hours. The reaction mixture was subjected to post-treatment and purification as in Example 1 to give 1.38 g of 4-hydroxy-2-propargyl-3-methyl-2-cyclopentenone. Yield, 91%.

Workup

  1. additionwas dropwise added
  2. customat 0° C
  3. additionAfter completion of the dropwise addition
  4. custompurification as in Example 1

Sources & evidence

ORD record
ord-5e86856ef5f9491a9c995f985afc21e8
Source dataset
uspto-grants-1986_08
Patent number
US04608442

Linked notes

Loading…