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

HRID 982227Notes

Reaction equation

HRID 982227 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-3eb4efb3b3cf42d7b5e0386c4c253654
Source dataset
uspto-grants-1991_02
Patent number
US04994479

Reaction notes

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