Trimethyl orthoformate → HCID 11356486, compound

HRID 1937761Notes

Reaction equation

HRID 1937761 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:16](=O)([O-])[O-:17].[Na+].[Na+]>>[CH3:1][O:2][C:3](=[O:8])[CH:4]([CH:9]([O:12][CH3:13])[O:10][CH3:11])[CH:5]([O:17][CH3:16])[O:6][CH3:7]

Participants

4

Reactant 3

HCID 9005Trimethyl orthoformateHCID 10340Sodium CarbonateHCID 5323651Methyl 3-methoxyacrylate

Product 1

HCID 11356486HCID 11356486, compoundYield 128.8%

Conditions

Temperature
40 °C

Procedure

To a stirred mixture of 17.7 g methyl-trans-3-methoxyacrylate and 32.3 g trimethyl ortho formate was added 0.4 g FeCl3. The mixture was heated to 40° C. for 24 hours, whereby 0.2 g FeCl3 were added every 6 hours. After cooling to room temperature, 5.00 g anhydrous sodium carbonate were added and the reaction mixture was stirred for 2 hours. Filtering, washing the filter-cake washed with trimethyl ortho formate and fractional distillation gave 13.5 g colorless liquid (80% of theoretical based on converted methyl-trans-3-methoxyacrylate) of boiling point 100° C./4 mm Hg. GC-analysis of the liquid revealed an assay of >99% (FID-detection).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationFiltering
  3. washwashing the filter-cake
  4. washwashed with trimethyl ortho formate and fractional distillation

Sources & evidence

ORD record
ord-5e4e7a16d59a4971870f7347a74db500
Source dataset
uspto-grants-2002_05
Patent number
US06395920B1

Reaction notes

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