Benzaldehyde → 2,2-Bis(hydroxymethyl)propane-1,3-diyl diprop-2-enoate

HRID 1649855Notes

Reaction equation

HRID 1649855 reaction equation
C1(C2[O:12][CH2:11][C:10]([CH2:19][O:20][C:21](=[O:24])[CH:22]=[CH2:23])([CH2:13][O:14][C:15](=[O:18])[CH:16]=[CH2:17])[CH2:9][O:8]2)C=CC=CC=1.COC1C=CC(O)=CC=1.C(O)(=O)C(O)=O.C(=O)([O-])[O-].[K+].[K+].C(=O)C1C=CC=CC=1>O>[C:15]([O:14][CH2:13][C:10]([CH2:19][O:20][C:21](=[O:24])[CH:22]=[CH2:23])([CH2:9][OH:8])[CH2:11][OH:12])(=[O:18])[CH:16]=[CH2:17]

Participants

7

Reactant 5

HCID 240BenzaldehydeHCID 971Oxalic AcidHCID 90154-MethoxyphenolHCID 11430Potassium CarbonateHCID 19854987HCID 19854987, compound

Product 1

HCID 932842,2-Bis(hydroxymethyl)propane-1,3-diyl diprop-2-enoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a two-liter flask equipped with an agitator, means for steam distillation, and a Claisen head with an efficient condenser was placed 664 g (2 moles) of 2-phenyl-5,5- bis(acryloyloxymethyl)-1,3-dioxane, two grams of 4-methoxyphenol and a hot solution of 8 grams of oxalic acid and 1.6 grams of potassium carbonate in 200 ml water. A slow stream of air was introduced into the steam inlet and the mixture stirred and warmed very slightly until the mixture appeared to be a homogeneous emulsion. Steam was then added to the air stream whereon benzaldehyde began to steam distill. It is desirable during the steam distillation that rapid stirring be maintained to provide intimate contact between the organic and aqueous layers in order to decrease the time required for hydrolysis as much as possible. After benzyaldehyde was no longer distilling, the still residue was cooled, saturated with sodium sulfate, filtered and extracted with ethyl acetate. The combined extracts were dried, preferably, by azeotropic distillation of water and ethyl acetate under reduced pressure. The 2,2-bis(acryloyloxymethyl)-1,3-propanediol obtained was a viscous, hydroscopic liquid. NMR spectroscopy confirmed the fact that no monol or triol was present in the product.

Workup

  1. customInto a two-liter flask equipped with an agitator
  2. distillationmeans for steam distillation
  3. customa Claisen head with an efficient condenser was placed
  4. additionA slow stream of air was introduced into the steam inlet
  5. temperaturewarmed very slightly until the mixture
  6. distillationdistill
  7. distillationIt is desirable during the steam distillation
  8. stirringthat rapid stirring
  9. temperaturebe maintained
  10. customto provide intimate contact between the organic and aqueous layers in order
  11. customrequired for hydrolysis as much as possible
  12. distillationAfter benzyaldehyde was no longer distilling
  13. temperaturethe still residue was cooled, saturated with sodium sulfate
  14. filtrationfiltered
  15. extractionextracted with ethyl acetate
  16. customThe combined extracts were dried
  17. distillationpreferably, by azeotropic distillation of water and ethyl acetate under reduced pressure

Sources & evidence

ORD record
ord-f1e4ff9de69942a2847938dc1b27a766
Source dataset
uspto-grants-1990_05
Patent number
US04921930

Reaction notes

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