Acetone → 1,3-Bis-(4-benzoyl-3-hydroxyphenoxy)-prop-2-yl 2-cyano-3,3-dimethylacrylate
Reaction equation
FC(F)(F)S(O)(=O)=O.[C:9]([CH2:11][C:12]([O:14][CH:15]([CH2:33][O:34][C:35]1[CH:40]=[CH:39][C:38]([C:41](=[O:48])[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[C:37]([OH:49])[CH:36]=1)[CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:20]([OH:32])[CH:19]=1)=[O:13])#[N:10].[CH3:50][C:51]([CH3:53])=O>>[C:9]([C:11](=[C:51]([CH3:53])[CH3:50])[C:12]([O:14][CH:15]([CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24](=[O:31])[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[C:20]([OH:32])[CH:19]=1)[CH2:33][O:34][C:35]1[CH:40]=[CH:39][C:38]([C:41](=[O:48])[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)=[C:37]([OH:49])[CH:36]=1)=[O:13])#[N:10]Participants
4
Conditions
- Temperature
- 56 °C
Procedure
1 g of trifluoromethanesulfonic acid was added to a solution of 55.2 g (0.1 mole) of 1,3-bis-(4-benzoyl-3-hydroxyphenoxy)-prop-2-yl cyanoacetate in 300 ml of acetone, and the solution was heated for 3 hours at a temperature of 56° C. After cooling to room temperature, the resulting crystalline precipitate was filtered off with suction and recrystallized from acetone. After drying, 51 g (86 percent of theory) of 1,3-bis-(4-benzoyl-3-hydroxyphenoxy)-prop-2-yl 2-cyano-3,3-dimethylacrylate were obtained in the form of colorless crystals having a melting point of 145° to 147° C. and a purity of 99 percent (HPLC). The structure of the compound obtained was confirmed by UV, IR and NMR spectra.
Workup
- temperatureAfter cooling to room temperature
- filtrationthe resulting crystalline precipitate was filtered off with suction
- customrecrystallized from acetone
- customAfter drying
Sources & evidence
- ORD record
- ord-d1be10188bd749ccb265edf5ad1c132b
- Source dataset
- uspto-grants-1989_04
- Patent number
- US04824892
Reaction notes
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