Hydrochloric Acid → Isopropyl chloro(oxo)acetate
Reaction equation
[CH3:1][CH:2]([OH:4])[CH3:3].[C:5](Cl)(=[O:9])[C:6]([Cl:8])=[O:7].Cl>>[Cl:8][C:6](=[O:7])[C:5]([O:4][CH:2]([CH3:3])[CH3:1])=[O:9]Participants
Procedure
The propan-2-ol (38.2 mL, 499 mmol) was added drop wise over 15 min to a cold (0° C.), nitrogen purged solution of oxalyl dichloride (101 g, 799 mmol) and the reaction was stirred at room temperature for 2.5 h. Then a reflux condenser was fitted and a slight vacuum was applied for about 1 h until HCl gas was removed (the HCl was trapped in by a sat'd solution of NaHCO3). The reflux condenser was removed and the flask was fitted with a short path distillation head. Excess reagent was removed by distillation under house vacuum (oil bath heated to 65° C.), and then the temperature was raised to between 85-95° C. and the product was distilled (NOTE: The 1st fraction of ˜5 mL was discarded) to provide isopropyl 2-chloro-2-oxoacetate 52.62 g (70%).
Workup
- customThen a reflux condenser was fitted
- customwas removed (the HCl
- customThe reflux condenser was removed
- customthe flask was fitted with a short path distillation head
- customExcess reagent was removed by distillation under house vacuum (oil bath heated to 65° C.)
- temperaturethe temperature was raised to between 85-95° C.
- distillationthe product was distilled (NOTE
Sources & evidence
- ORD record
- ord-f0ee45c26174411e82fbfe48077a8d9b
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193720B2
Reaction notes
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