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

HRID 595244Notes

Reaction equation

HRID 595244 reaction equation
[OH:1][CH2:2][CH:3]([CH2:5][OH:6])[OH:4].[CH:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>S(=O)(=O)(O)O.C1(C)C=CC=CC=1>[C:8]1([CH:7]2[O:6][CH2:5][CH:3]([OH:4])[CH2:2][O:1]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 753GlycerolHCID 962Water

Product 1

HCID 743621,3-Dioxan-5-ol, 2-phenyl-

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 1140TolueneSolvent

Procedure

Concentrated sulfuric acid (3 drops) was added to a mixture of glycerol (55.1 g, 0.60 mmol) and benzaldehyde (50.0 g, 0.47 mmol) in toluene (69 mL) and the resulting mixture was heated to reflux in a Dean-Stark water separator under nitrogen. When the separation of water was complete, the solvent was concentrated under reduced pressure to give a white solid which was recrystallized from ether/petroleum ether. Repeated recrystallization from the same solvent gave pure 2-phenyl-1,3-dioxan-5-ol. 1H NMR (300 MHz, CDCl3) δ 7.51-7.48 (m, 2H), 7.41-7.37 (m, 3H), 5.55 (s, 1H), 4.21-4.17 (m, 2H), 4.14-4.10 (m, 2H), 3.63 (s, 1H), 2.78 (bs, 1H).

Workup

  1. temperaturethe resulting mixture was heated
  2. customWhen the separation of water
  3. concentrationthe solvent was concentrated under reduced pressure
  4. customto give a white solid which
  5. customwas recrystallized from ether/petroleum ether
  6. customrecrystallization from the same solvent

Sources & evidence

ORD record
ord-938ebd134891465cad1df953466748b3
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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