Peracetic Acid → 4,5-Anhydro-1,3-dideoxy-4-methyl-3-prop-2-en-1-ylpent-2-ulose

HRID 894160Notes

Reaction equation

HRID 894160 reaction equation
C([O-])(=[O:3])C.[Na+].[CH2:6]([CH:9]([C:13]([CH3:15])=[CH2:14])[C:10](=[O:12])[CH3:11])[CH:7]=[CH2:8].C(OO)(=O)C>ClCCl>[CH2:6]([CH:9]([C:13]1([CH3:15])[O:3][CH2:14]1)[C:10](=[O:12])[CH3:11])[CH:7]=[CH2:8]

Participants

5

Reactant 3

HCID 6585Peracetic AcidHCID 517045Sodium AcetateHCID 132086223-(Prop-1-en-2-yl)hex-5-en-2-one

Product 1

HCID 132086284,5-Anhydro-1,3-dideoxy-4-methyl-3-prop-2-en-1-ylpent-2-ulose

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

2.5 Grams of sodium acetate was added at 30° C. to a mixture of 3-allyl-4-methyl-pent-4-en-2-one (5.0 g) and dichloromethane (100 ml), and then a 9% peracetic acid solution (153 g) was added dropwise thereto over 1 hour. After stirring at 30° C. for 4 hours, the reaction solution was treated in the same manner as in Example 3 to obtain 1.20 g of pure 3-allyl-4-methyl-4,5-epoxy-pentan-2-one.

Workup

  1. additionthe reaction solution was treated in the same manner as in Example 3

Sources & evidence

ORD record
ord-78c9b39f1d064d6daa6d24f94f44e9ea
Source dataset
uspto-grants-1981_08
Patent number
US04282372

Reaction notes

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