Isopropanol → 1-Methylethyl 2-methoxyacetate

Temperature

25 °C

434.1 g (4.0 mol) of methyl chloroacetate are initially introduced and stirred at 25° C. 756.3 g (4.2 mol) of 30% strength sodium methoxide solution are added dropwise in the course of 2.5 h such that a reaction temperature of 65° C. is not exceeded. After the addition, stirring is continued at reflux temperature for a further 3 h. 436.0 g of methanol are then removed from the reaction mixture by distillation. 480.8 g (8 mol) of isopropanol are added to the residue and the mixture is heated under reflux. In the course of this, methanol is removed via a 0.5 m long Multifil column at a reflux ratio of approximately 1:1 (244.4 g of distillate). After 6.5 h, the conversion of the methyl methoxyacetate to the isopropyl methoxyacetate is >98%. After cooling, the reaction mixture is concentrated to dryness on a rotary evaporator at a maximum bath temperature of 120° C. and a pressure of <15 mbar. A residue of 274.3 g and a distillate of 668.0 g are obtained. The distillate is fractionated through a 0.5 m long Multifil column. Isopropyl methoxyacetate is obtained as the main fraction (390.6 g, yield 74%) with a purity of >99%, a chlorine content of 10 ppm and a water content of <0.05%.

1. additionAfter the addition
2. stirringstirring
3. temperatureat reflux temperature for a further 3 h
4. custom436.0 g of methanol are then removed from the reaction mixture by distillation
5. temperaturethe mixture is heated
6. temperatureunder reflux
7. customIn the course of this, methanol is removed via a 0.5 m long Multifil column at a reflux ratio of approximately 1:1 (244.4 g of distillate)
8. temperatureAfter cooling
9. concentrationthe reaction mixture is concentrated to dryness on a rotary evaporator at a maximum bath temperature of 120° C.
10. customA residue of 274.3 g and a distillate of 668.0 g are obtained

ORD record

ord-b93a55a466b24849a79d5926ea9fa2af

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06143920