4-Nitrobenzaldehyde → 5-Acetyl-5-methyl-2-(4-nitrophenyl)-1,3-dioxane

HRID 892401Notes

Reaction equation

HRID 892401 reaction equation
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH3:7])[C:4](=[O:6])[CH3:5].[N+:10]([C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1)([O-:12])=[O:11].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[C:4]([C:3]1([CH3:7])[CH2:8][O:9][CH:17]([C:16]2[CH:19]=[CH:20][C:13]([N+:10]([O-:12])=[O:11])=[CH:14][CH:15]=2)[O:1][CH2:2]1)(=[O:6])[CH3:5]

Participants

6

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 5365163,3-Bis(hydroxymethyl)-2-butanone

Product 1

HCID 130050175-Acetyl-5-methyl-2-(4-nitrophenyl)-1,3-dioxane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3,3-bis(Hydroxymethyl)-2-butanone (39.7 parts) and 4-nitrobenzaldehyde (30.2 parts) are combined in toluene (300 parts) containing p-toluenesulfonic acid, (p-TSA), (1.0 part) and the mixture held under reflux until a theoretical amount of water is removed by a Dean-Stark moisture trap. The solution is concentrated in vacuo and the residue washed once with dilute sodium bicarbonate solution. The product is recrystallized from ethyl acetate-heptane mixed solvent to give colorless needles, m.p. 101-102.5° C. Proton NMR and combustion analysis are consistent with those values predicted for the desired product. Combustion Analysis for C13H15NO5 --Calculated: C, 58.9%; H, 5.7%; N, 5.3%. Found: C, 59.0%; H, 5.8%; N, 5.4%.

Workup

  1. customis removed by a Dean-Stark moisture trap
  2. concentrationThe solution is concentrated in vacuo
  3. washthe residue washed once with dilute sodium bicarbonate solution
  4. customThe product is recrystallized from ethyl acetate-heptane mixed solvent
  5. customto give colorless needles, m.p. 101-102.5° C

Sources & evidence

ORD record
ord-f8d6fd28b2634e6bbda42360e24074e3
Source dataset
uspto-grants-1992_06
Patent number
US05118599

Reaction notes

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