p-Toluenesulfonic acid → HCID 10944078, compound

HRID 250525Notes

Reaction equation

HRID 250525 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)=[O:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:24](O)[CH2:25][CH2:26][OH:27]>C1(C)C=CC=CC=1>[N+:10]([C:7]1[CH:6]=[CH:5][C:4]([C:2]2([CH3:1])[O:27][CH2:26][CH2:25][CH2:24][O:3]2)=[CH:9][CH:8]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7487p-NitroacetophenoneHCID 104421,3-Propanediol

Product 1

HCID 10944078HCID 10944078, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-nitroacetophenone (1.65 g, 10.0 mmol), p-toluenesulfonic acid (172 mg, 1.00 mmol) and 1,3-propanediol (2.3 mL, 30 mmol) in dry toluene (20 mL) was heated at reflux with a Dean-Stark apparatus under nitrogen for 24 h. The mixture was allowed to cool to room temperature and the solvent was evaporated in vacuo. The residue was taken up in ether (20 mL) and the solution was washed with saturated sodium bicarbonate solution (2×10 mL) and brine (1×10 mL), then dried (Na2SO4) and concentrated under reduced pressure. Recrystallisation from ether and hexane afforded 2-(4-nitrophenyl)-2-methyl-1,3-dioxane (26) as a pale yellow crystals (1.60 g, 72%; yield based from the first crop of crystals). 1H nmr (300 MHz, CDCl3) 1.52 (s, 3H, CH3), 2.08-2.22 (m, 2H, OCH2CH2CH2O), 3.65-3.80 (m, 2H, OCH2), 3.88-4.00 (m, 2H, OCH2), 7.63 (d, J=8.9 Hz, 2H, 2×ArH), 8.26 (d, J=8.9 Hz, 2H, 2×ArH).

Workup

  1. temperaturewas heated
  2. temperatureat reflux with a Dean-Stark apparatus under nitrogen for 24 h
  3. customthe solvent was evaporated in vacuo
  4. washthe solution was washed with saturated sodium bicarbonate solution (2×10 mL) and brine (1×10 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customRecrystallisation from ether and hexane

Sources & evidence

ORD record
ord-743171c7634744b0b79808ffcdcabf0d
Source dataset
uspto-grants-2011_01
Patent number
US07863313B2

Reaction notes

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