Butanedione → 1-(1,4-Dioxan-2-yl)ethan-1-one

Reaction equation

[C:1]([C:4]([CH3:6])=[O:5])([CH3:3])=[O:2].[OH-].[Na+].[O:9]1CCO[CH2:11][CH2:10]1>>[O:2]1[CH2:11][CH2:10][O:9][CH2:3][CH:1]1[C:4](=[O:5])[CH3:6]

Participants

Reactant 3

HCID 650Butanedione

HCID 14798Sodium Hydroxide

HCID 312751,4-Dioxane

Product 1

HCID 543451261-(1,4-Dioxan-2-yl)ethan-1-oneYield 36%

Conditions

Temperature: 0 °C

Procedure

To a solution of benzoic peroxide (20 g, 141 mmol) in 200 mL 1,4-dioxane at room temperature under nitrogen atmosphere was added biacetyl (24.3 g, 282 mmol). After the addition, the mixture was heated to reflux and stirred for 24 hours. The reaction mixture was cooled to 0° C. The pH was adjusted to around 9 by progressively adding 2N sodium hydroxide below 0° C., extracted with 2-methoxy-2-methylpropane (10 mL×3), and concentrated to give 1-(1,4-dioxan-2-yl)ethanone (13 g, 36%) as a yellow oil which was used directly in the next step without purification.