2,2-Dimethyl-1,3-dioxane-4,6-dione → 1,3-Dioxane-4,6-dione, 5-[(4-bromophenyl)methylene]-2,2-dimethyl-

HRID 600306Notes

Reaction equation

[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C:11]1([CH3:19])[O:16][C:15](=[O:17])[CH2:14][C:13](=[O:18])[O:12]1>[Br-].C[N+](C)(C)CCCCCCCCCCCCCCCC>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:14]2[C:15](=[O:17])[O:16][C:11]([CH3:19])([CH3:10])[O:12][C:13]2=[O:18])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of N,N,N-trimethylhexadecan-1-aminium bromide (15.76 g), 4-bromobenzaldehyde (80 g) and 2,2-dimethyl-1,3-dioxane-4,6-dione (68.6 g) was heated and stirred at 60° C. for 1 h, during which time a solid precipitated from solution. The mixture was allowed to cool to room temperature. The solid was collected by filtration and washed with cold water (600 mL). dried in vacuo at 50° C. to give 5-(4-bromobenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (108 g) as a colourless solid.

Workup

temperaturewas heated
customprecipitated from solution
temperatureto cool to room temperature
filtrationThe solid was collected by filtration
washwashed with cold water (600 mL)
customdried in vacuo at 50° C.

Sources & evidence

ORD record: ord-bd7f36dbf1784722a51abaae17641df6
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902181B2

Reaction notes

Loading…