Formaldehyde → Methyl tropate

HRID 2255275Notes

Reaction equation

HRID 2255275 reaction equation
[C:1](=O)(O)[O-:2].[Na+].C=O.[C:8]1([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CS(C)=O>[C:15]([O:17][CH3:18])(=[O:16])[CH:14]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:1][OH:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 7559Methyl phenylacetateHCID 516892Sodium Bicarbonate

Product 1

HCID 239086Methyl tropateYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A three necked one-liter flask equipped with a drying tube, a thermometer and a stopper was flame-dried, cooled and then charged with sodium bicarbonate (2.1 g; 0.025 mole), paraformaldehyde (34.74 g; 1.1 mole) and 300 mL of dimethylsulfoxide (DMSO). The air in the flask was purged with dry nitrogen and methyl phenylacetate (150:18 g; 1 mole) was added in one portion. Residual ester was washed into the flask using dry DMSO (5 mL). The slurry was then stirred magnetically (initial temperature 22°-23° C.) and the temperature rose slowly over one hour to 33° C. The temperature remained at about 32°-33° C. for 1.5 hrs. at which time the reaction liquid was almost a clear solution. The temperature was then raised to 45°-46° C. over 30 min. and kept at this temperature for 12 hrs. The solution was then allowed to cool and left at room temperature for 9 hrs. The reaction mixture was clear and essentially colorless with only a small amount of a white solid appearing at the bottom of the flask. NMR analysis of the solution indicated approximately an 80% yield of methyl tropate.

Workup

  1. customA three necked one-liter flask equipped with a drying tube
  2. customa thermometer and a stopper was flame-dried
  3. temperaturecooled
  4. additionwas added in one portion
  5. washResidual ester was washed into the flask
  6. customat which time the reaction liquid
  7. temperatureThe temperature was then raised to 45°-46° C. over 30 min.
  8. waitkept at this temperature for 12 hrs
  9. temperatureto cool
  10. waitleft at room temperature for 9 hrs

Sources & evidence

ORD record
ord-85bda8bf48e24d0b9b1be178d7b766ad
Source dataset
uspto-grants-1993_08
Patent number
US05239121

Reaction notes

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