p-Toluenesulfonic acid → HCID 118023273, compound

HRID 522673Notes

Reaction equation

HRID 522673 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:13])[CH2:11][OH:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].CO[C:16](OC)([CH3:18])[CH3:17].CC1C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH3:17][C:16]1([CH3:18])[O:13][CH:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:11][O:12]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 41172001-(4-nitrophenyl)ethane-1,2-diol

Product 1

HCID 118023273HCID 118023273, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 1-(4-nitrophenyl)ethane-1,2-diol (7.0 g, 38.3 mmol), 2,2-dimethoxypropane (16 g, 153.2 mmol) and 4-methylbenzenesulfonic acid (2.6 g, 15.32 mmol) in acetone (100 mL) was stirred at 25° C. for 12 h. The reaction mixture was concentrated and then dissolved in ethyl acetate (300 mL). The organic layer was separated, washed by water (100 mL) and brine (100 mL), dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=5/1) to afford the title compound (4.0 g, 40%) as a yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in ethyl acetate (300 mL)
  3. customThe organic layer was separated
  4. washwashed by water (100 mL) and brine (100 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-75456e14d3b24a13a9bd7dd04842bf38
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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