Water → Chrysanthemic Acid

HRID 542989

Reaction equation

HRID 542989 reaction equation
[CH3:1][C:2]([CH3:12])=[CH:3][C@H:4]1[C:6]([CH3:8])([CH3:7])[C@H:5]1[C:9]([OH:11])=[O:10].O>O1CCOCC1.C(OO)(C)(C)C.[Br-].[Al+3].[Br-].[Br-]>[CH3:1][C:2]([CH3:12])=[CH:3][CH:4]1[C:6]([CH3:7])([CH3:8])[CH:5]1[C:9]([OH:11])=[O:10]

Participants

6

Reactant 2

HCID 962WaterHCID 20755Chrysanthemic acid, cis-(-)-

Product 1

HCID 2743Chrysanthemic AcidYield 95.5%

Reagents, catalysts & solvents 3

HCID 6410tert-Butyl hydroperoxideCatalystHCID 166749BromhydrolCatalystHCID 312751,4-DioxaneSolvent2×

Procedure

In a 50 ml flask, there were charged (-)-cis-chrysanthemic acid (2.0 g), dioxane (17.5) and t-butyl hydroperoxide (0.011 g) under nitrogen. A solution of aluminum bromide (0.032 g) in dioxane (0.5 g) was added thereto at 15°-20° C. with stirring. After 30 minutes, water (0.5 g) was added to the reaction mixture with stirring. The reaction mixture was treated in the same manner as described in Example 1 and 1.91 g of chrysanthemic acid was obtained. The composition was as follows: (+)-cis, 3.3%; (-)-cis, 4.2%; (+)-trans, 46.2%; (-)-trans, 46.2%.

Workup

  1. stirringwith stirring
  2. additionThe reaction mixture was treated in the same manner

Sources & evidence

ORD record
ord-8736bbb119b442fea09ceae2ca173bdd
Source dataset
uspto-grants-1987_04
Patent number
US04659864

Linked notes

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