Dimethyl Ether → HCID 11356486, compound

HRID 1937763Notes

Reaction equation

HRID 1937763 reaction equation
[CH3:1][O:2][C:3](=[O:8])/[CH:4]=[CH:5]/[O:6][CH3:7].[CH:9](OC)([O:12][CH3:13])[O:10][CH3:11].C[O-].[Na+].[CH3:19][O:20]C>>[CH3:1][O:2][C:3](=[O:8])[CH:4]([CH:9]([O:12][CH3:13])[O:10][CH3:11])[CH:5]([O:20][CH3:19])[O:6][CH3:7]

Participants

5

Reactant 4

HCID 8254Dimethyl EtherHCID 9005Trimethyl orthoformateHCID 5323651Methyl 3-methoxyacrylateHCID 10942334Sodium Methoxide

Product 1

HCID 11356486HCID 11356486, compoundYield 80%

Procedure

To a stirred mixture of 116.0 g methyl-trans-3-methoxyacrylate and 530.0 g trimethyl ortho formate were added 5.0 g FeCl3. The mixture was heated to 35° C. for 30 hours with an additional 1.0 g FeCl3 being added every 6 hours. The mixture was cooled to room temperature and neutralized by addition of 30% sodium methylate solution. After stirring for 2 hours, 30.0 g PEG-dimethylether (mg=1000) were added. The trimethyl ortho formate excess was recovered by fractional distillation. Flash-distillation of the remaining material gave 155.4 g colorless liquid (80% of theoretical based on converted methyl-trans-3-methoxyacrylate) of boiling point 100° C./4 mm Hg. A GC-analysis of the liquid revealed an assay of >99% (FID-detection).

Workup

  1. additionadded every 6 hours
  2. distillationThe trimethyl ortho formate excess was recovered by fractional distillation
  3. distillationFlash-distillation of the remaining material

Sources & evidence

ORD record
ord-59edeed3b53b4bf6b1651a4036d4eaa6
Source dataset
uspto-grants-2002_05
Patent number
US06395920B1

Reaction notes

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