p-Toluenesulfonic acid → 2,2,4,4-Tetramethyl-5-(4-nitrophenyl)-1,3-dioxolane

HRID 522670Notes

Reaction equation

HRID 522670 reaction equation
[CH3:1][C:2]([OH:15])([CH3:14])[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)[OH:4].CO[C:18](OC)([CH3:20])[CH3:19].CC1C=CC(S(O)(=O)=O)=CC=1.CC(=O)OCC>CC(C)=O>[CH3:19][C:18]1([CH3:20])[O:15][C:2]([CH3:1])([CH3:14])[CH:3]([C:5]2[CH:6]=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=2)[O:4]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 8857Ethyl AcetateHCID 916193172-Methyl-1-(4-nitrophenyl)propane-1,2-diol

Product 1

HCID 1180219762,2,4,4-Tetramethyl-5-(4-nitrophenyl)-1,3-dioxolaneYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-methyl-1-(4-nitrophenyl)propane-1,2-diol (1.5 g, 7.1 mmol), 2,2-dimethoxypropane (1.45 g, 14.2 mmol) and TsOH (cat., 260 mg, 1.5 mmol) in acetone (40 mL) was stirred at 30° C. for 16 h. The reaction mixture was concentrated. The residue was purified by silica gel chromatography, eluting with PE:EA (8:1), to obtain the desired product (1.5 g, 85% yield) as a white solid. 1H-NMR (500 MHz, CDCl3) δ ppm 8.23 (d, 2H, J=9.0 Hz), 7.57 (d, 2H, J=9.0 Hz), 4.93 (s, 1H), 1.59 (s, 3H), 1.48 (s, 3H), 1.46 (s, 3H), 0.78 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe residue was purified by silica gel chromatography
  3. washeluting with PE

Sources & evidence

ORD record
ord-3870364321b44d6eba1bfbbc6106fae8
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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