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.CC1(C)CCCC(C)(C)[NH+]1[O-]>ClCCl>[CH3:8][C:3]([CH3:9])([CH:2]=[O:1])[C:4]([O:6][CH3:7])=[O:5]Participants
Conditions
- Temperature
- 0 °C
Procedure
Methyl 3-hydroxy-2,2-dimethyl-propanoate (52.4 g, 396.49 mmol) is dissolved in dichloromethane (495 mL) and the mixture is cooled in an ice-water bath. Trichloroisocyanuric acid (101.36 g, 436.14 mmol) is added portionwise, followed by 2,2,6,6-tetramethylpiperidine-N-oxide (6.20 g, 39.65 mmol). The mixture is stirred at 0° C. for 15 min and then allowed to warm to RT and stirred for an additional 60 min. The solid is then filtered through CELITE® and rinsed with dichloromethane (300 mL). The filtrate is washed with a saturated solution of Na2CO3 in water. The organic phase is dried over Na2SO4, filtered, and concentrated under reduced pressure to afford the title compound (41.24 g, 80%) as a greenish oil. The product is used without further purification in the next reaction step. 1H NMR (400 MHz, CDCl3); δ 1.34 (6H, s), 1.34 (6H, s), 3.74 (3H, s), 9.64 (1H, s).
Workup
- temperaturethe mixture is cooled in an ice-water bath
- temperatureto warm to RT
- stirringstirred for an additional 60 min
- filtrationThe solid is then filtered through CELITE®
- washrinsed with dichloromethane (300 mL)
- washThe filtrate is washed with a saturated solution of Na2CO3 in water
- dry with materialThe organic phase is dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d2618185fc0d419cb12f79dea2e41456
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08288548B2
Reaction notes
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