Benzaldehyde → 1,3-Dioxan-5-ol, 2-phenyl-

HRID 1761736Notes

Reaction equation

HRID 1761736 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][CH2:10][CH:11]([CH2:13]O)[OH:12]>C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:2]1([CH:1]2[O:9][CH2:10][CH:11]([OH:12])[CH2:13][O:8]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 753Glycerol

Product 1

HCID 743621,3-Dioxan-5-ol, 2-phenyl-Yield 21.1%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Conditions

Temperature
0 °C

Procedure

A mixture of about 184 g of glycerol, about 212.03 g of benzaldehyde and about 3.6 g of p-toluenesulfonic acid was refluxed for about 5 hours, using a Dean-Stark trap. The mixture was then cooled at about 0° C. for about 17 hours and the solid collected and dissolved in about 1200 ml of warm toluene containing about one gram of sodium methoxide. This solution was washed with about 600 ml of dilute (about 1%) dibasic sodium phosphate and dried. Dilution with petroleum ether gave a solid which was recrystallized from toluene-petroleum ether, giving about 76 g of the desired title compound as a white solid.

Workup

  1. temperaturewas refluxed for about 5 hours
  2. customthe solid collected
  3. dissolutiondissolved in about 1200 ml of warm toluene containing about one gram of sodium methoxide
  4. washThis solution was washed with about 600 ml
  5. additionof dilute (about 1%) dibasic sodium phosphate
  6. customdried
  7. customDilution with petroleum ether gave a solid which
  8. customwas recrystallized from toluene-petroleum ether

Sources & evidence

ORD record
ord-5a38764008b3437794aaf7d433bc72d3
Source dataset
uspto-grants-1989_05
Patent number
US04827011

Reaction notes

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