Trichloroisocyanuric Acid → Methyl 2,2-dimethyl-3-oxopropanoate
Reaction equation
[OH:1][CH2:2][C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5].ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O>ClCCl>[CH3:8][C:3]([CH3:9])([CH:2]=[O:1])[C:4]([O:6][CH3:7])=[O:5]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 2.5 °C
Procedure
Methyl 3-hydroxy-2,2-dimethyl-propanoate (25.4 kg, 192.2 mol) and dichloromethane (241 L) are combined under a nitrogen atmosphere at RT with stirring. (2,2,6,6-Tetramethyl-piperidin-1-yl)oxyl (0.61 kg, 3.9 mol) is added and the reaction mixture is cooled to 0-5° C. Trichloroisocyanuric acid (31.2 kg, 134.5 mol) is added portionwise at 0-5° C. and the reaction mixture is stirred for 16-18 h at this temperature. The reaction is filtered and the filtercake is washed with dichloromethane (25.4 L) and the filtrate concentrated under reduced pressure below 50° C. 1,4-Dioxane (25.4 L) is added and the organic phase is concentrated under reduced pressure below 65° C. to obtain the title compound as a yellow liquid (127.8 kg, 77%) that is used without further purification.
Workup
- customare combined under a nitrogen atmosphere at RT
- addition(2,2,6,6-Tetramethyl-piperidin-1-yl)oxyl (0.61 kg, 3.9 mol) is added
- stirringthe reaction mixture is stirred for 16-18 h at this temperature
- filtrationThe reaction is filtered
- washthe filtercake is washed with dichloromethane (25.4 L)
- concentrationthe filtrate concentrated under reduced pressure below 50° C
- addition1,4-Dioxane (25.4 L) is added
- concentrationthe organic phase is concentrated under reduced pressure below 65° C.
Sources & evidence
- ORD record
- ord-1f50a740b7894a0eaf713542664c7167
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08288548B2
Reaction notes
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