Hydrochloric Acid → 2-Cyclopenten-1-one, 4-hydroxy-3-methyl-2-(2-propen-1-yl)-

HRID 365170Notes

Reaction equation

HRID 365170 reaction equation
Cl.[CH2:2]([CH:5]1[C:9](OC(=O)C)([CH3:10])[CH:8]=[CH:7][C:6]1=[O:15])[CH:3]=[CH2:4].[O:16]1CCOCC1>>[CH2:2]([C:5]1[C:6](=[O:15])[CH2:7][CH:8]([OH:16])[C:9]=1[CH3:10])[CH:3]=[CH2:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 13335393HCID 13335393, compound

Product 1

HCID 110832-Cyclopenten-1-one, 4-hydroxy-3-methyl-2-(2-propen-1-yl)-

Procedure

In the same flask as in Example 1, 10% aqueous hydrochloric acid (10 ml) and dioxane (10 ml) were charged, and 2-allyl-3-acetoxy-3-methyl-4-cyclopentenone (1.94 g) was dropwise added thereto in 2 hours while keeping the inner temperature at 0° to 10° 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 1.37 g of 2-allyl-3-methyl-4-hydroxy-2-cyclopentenone. Yield, 90%.

Workup

  1. customat 0° to 10° C
  2. additionAfter completion of the dropwise addition
  3. custompurification as in Example 1

Sources & evidence

ORD record
ord-0732735f07a1462ebad7a632a59fab4a
Source dataset
uspto-grants-1986_08
Patent number
US04608442

Reaction notes

Loading…