1,3-Propanediol → 4-(1,3-Dioxan-2-yl)-2-nitrophenol

HRID 847289Notes

Reaction equation

HRID 847289 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH2:13](O)[CH2:14][CH2:15][OH:16].C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C=CC=CC=1>[O:7]1[CH2:13][CH2:14][CH2:15][O:16][CH:6]1[C:5]1[CH:8]=[CH:9][C:2]([OH:1])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1

Participants

5

Reactant 3

HCID 104421,3-PropanediolHCID 181694-Hydroxy-3-nitrobenzaldehydeHCID 22033616Pyridinium.p-toluenesulfonate

Product 1

HCID 5972564-(1,3-Dioxan-2-yl)-2-nitrophenolYield 85.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 8 g of 4-hydroxy-3-nitrobenzaldehyde,16 g of 1,3-propanediol, a catalytic amount of pyridinium p-toluenesulfonic acid and 250 ml of toluene was azeotropically dehydrated with heating under reflux. The reaction mixture was cooled, washed with water, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was recrystallized from toluene-n-hexane to obtain 9.2 g of 4-(1,3-dioxan-2-yl)-2-nitrophenol.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. temperatureThe reaction mixture was cooled
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from toluene-n-hexane

Sources & evidence

ORD record
ord-06936f6bc1254764b66eb43fd9d8d99c
Source dataset
uspto-grants-1992_08
Patent number
US05140046

Reaction notes

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