Water → 2,2-Dimethyl-5,5-bis(4-nitrobenzyl)-1,3-dioxane-4,6-dione

HRID 2090145Notes

Reaction equation

[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:12][C:13]1([CH3:21])[O:20][C:18](=[O:19])[CH2:17][C:15](=O)O1.[C:22](=[O:25])([O-:24])[O-].[K+].[K+].[OH2:28]>CC(=O)CC>[CH3:21][C:13]1([CH3:12])[O:24][C:22](=[O:25])[C:17]([CH2:15][C:7]2[CH:10]=[CH:11][C:4]([N+:1]([O-:2])=[O:28])=[CH:5][CH:6]=2)([CH2:8][C:7]2[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[C:18](=[O:19])[O:20]1

Participants

Conditions

Temperature: 50 °C

Procedure

15.0 g (69.4 mmol) of 4-nitrobenzylbromide and 5.00 g (34.7 mmol) of Meldrum's acid were dissolved in 100 ml 2-butanone. 4.40 g (104.1 mmol) potassium carbonate were added, the resulting suspension was heated to 50° C. and allowed to react for 2.5 hours. After cooling to room temperature, 100 ml water were added. The product was collected by filtration and washed with a lot of water. 12.3 g (85%) of 2,2-dimethyl-5,5-bis(4-nitrobenzyl)-1,3-dioxane-4,6-dione as yellowish powder was used without further purification.

Workup

customto react for 2.5 hours
temperatureAfter cooling to room temperature
filtrationThe product was collected by filtration
washwashed with a lot of water
custom12.3 g (85%) of 2,2-dimethyl-5,5-bis(4-nitrobenzyl)-1,3-dioxane-4,6-dione as yellowish powder was used without further purification

Sources & evidence

ORD record: ord-af6ba1866b1544f2a5461bffba4c4835
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436132B2

Reaction notes

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