Trimethyl orthoformate → HCID 11356486, compound

HRID 1937762Notes

Reaction equation

HRID 1937762 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+]>C1([Sn](Cl)(Cl)Cl)C=CC=CC=1>[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

5

Reactant 3

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

Product 1

HCID 11356486HCID 11356486, compoundYield 110.6%

Reagents, catalysts & solvents 1

HCID 14298Monophenyltin trichlorideCatalyst

Conditions

Temperature
60 °C

Procedure

To a stirred mixture of 17.7 g methyl-trans-3-methoxyacrylate and 32.3 g trimethyl ortho formate was added 1.0 g PhSnCl3. The mixture was heated to 60° C. for 24 hours, cooled to room temperature and 5.00 g anhydrous sodium carbonate were added. After stirring for 2 hours, the mixture was filtered and the filter-cake washed with trimethyl ortho formate. Fractional distillation gave 11.6 g colorless liquid (69% of theoretical based on converted methyl-trans-3-methoxyacrylate) of boiling point 1000° C./4 mm Hg, A GC-analysis of the liquid revealed an assay of >99% (FID-detection).

Workup

  1. temperaturecooled to room temperature
  2. filtrationthe mixture was filtered
  3. washthe filter-cake washed with trimethyl ortho formate
  4. distillationFractional distillation

Sources & evidence

ORD record
ord-2bc0b58f93c547ffb2604a6991478d12
Source dataset
uspto-grants-2002_05
Patent number
US06395920B1

Reaction notes

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