Isopropanol → 1-Methylethyl 2-methoxyacetate

HRID 1857074Notes

Reaction equation

HRID 1857074 reaction equation
Cl[CH2:2][C:3]([O:5][CH3:6])=O.C[O-:8].[Na+].[CH:10]([OH:13])([CH3:12])[CH3:11].ClCl>O>[CH3:6][O:5][CH2:3][C:2]([O:13][CH:10]([CH3:12])[CH3:11])=[O:8]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 7295Methyl chloroacetateHCID 24526ChlorineHCID 10942334Sodium Methoxide

Product 1

HCID 5421921-Methylethyl 2-methoxyacetateYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

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. 407.5 g of methanol are then separated 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 through a 0.5 m long Multifil column at a reflux ratio of approximately 1:1 (291.9 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 filtered off with suction and the residue is washed with 450 g of isopropanol. A residue of 412.1 g and a liquid phase (filtrate and wash liquid) of 969.9 g are obtained. The liquid phase is fractionated through a 0.5 m long Multifil column. Isopropyl methoxyacetate (405.0 g, yield 77%) with an organic purity of >99%, a chlorine content of 10 ppm and a water content of <0.05% is obtained as the main fraction.

Workup

  1. additionAfter the addition
  2. stirringstirring
  3. temperatureat reflux temperature for a further 3 h
  4. custom407.5 g of methanol are then separated from the reaction mixture by distillation
  5. temperaturethe mixture is heated
  6. temperatureunder reflux
  7. customIn the course of this, methanol is removed through a 0.5 m long Multifil column at a reflux ratio of approximately 1:1 (291.9 g of distillate)
  8. temperatureAfter cooling
  9. filtrationthe reaction mixture is filtered off with suction
  10. washthe residue is washed with 450 g of isopropanol
  11. washA residue of 412.1 g and a liquid phase (filtrate and wash liquid) of 969.9 g
  12. customare obtained

Sources & evidence

ORD record
ord-830697164340421fa8ea6ff82b6bb81e
Source dataset
uspto-grants-2000_11
Patent number
US06143920

Reaction notes

Loading…