1-Octanol → Octyl 2-methoxyacetate

HRID 1857076Notes

Reaction equation

HRID 1857076 reaction equation
ClCC(OC)=O.C[O-].[Na+].[CH3:10][O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14].[CH2:17](O)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]C>>[CH3:10][O:11][CH2:12][C:13]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:14]

Participants

5

Reactant 4

HCID 9571-Octanol2×HCID 7295Methyl chloroacetateHCID 80507Methyl methoxyacetateHCID 10942334Sodium Methoxide

Product 1

HCID 542206Octyl 2-methoxyacetateYield 74%

Conditions

Temperature
25 °C

Procedure

537.2 g (4.95 mol) of methyl chloroacetate are initially introduced and stirred at 25° C. 936.4 g (5.2 mol) of 30% strength sodium methoxide solution are added dropwise in the course of 2.5 h such that a reaction temperature of 65° is not exceeded. After the addition, stirring is continued at reflux temperature for a further 3 h. 511.9 g of methanol are then removed from the reaction mixture by distillation. 1,289.3 g (9.9 mol) of n-octanol 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 (303.5 g of distillate), the bottom temperature rising to 210° C. during the removal. After 6.5 h, the conversion of the methyl methoxyacetate to the n-octyl methoxyacetate is >98%. The reaction mixture is fractionated through a 0.5 m long Multifil column. Initially, n-octanol and methyl methoxyacetate are distilled off n-Octyl methoxyacetate (740.0 g, yield 74%) is then obtained as a main fraction with a purity >99%, a chlorine content of 10 ppm and a water content of <0.05%.

Workup

  1. additionAfter the addition
  2. stirringstirring
  3. temperatureat reflux temperature for a further 3 h
  4. custom511.9 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 through a 0.5 m long Multifil column at a reflux ratio of approximately 1:1 (303.5 g of distillate)
  8. customthe bottom temperature rising to 210° C. during the removal

Sources & evidence

ORD record
ord-9da746758ef247f580a79c9e1580237f
Source dataset
uspto-grants-2000_11
Patent number
US06143920

Reaction notes

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