Ethylene Glycol → HCID 59764583, compound

HRID 388552Notes

Reaction equation

HRID 388552 reaction equation
[CH:1]([O:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([C:14](=[O:16])[CH3:15])=[C:7]([CH3:17])[CH:6]=1)([CH3:3])[CH3:2].[CH2:18](O)[CH2:19][OH:20].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.C(OCC)(=O)C>[CH:1]([O:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([C:14]2([CH3:15])[O:20][CH2:19][CH2:18][O:16]2)=[C:7]([CH3:17])[CH:6]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 67071160HCID 67071160, compound

Product 1

HCID 59764583HCID 59764583, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(4-Isopropoxy-2-methyl-5-nitro-phenyl)-ethanone (0.788 g, 3.32 mmol), ethyleneglycol (1.8 mL), and p-toluenesulfonic acid monohydrate (6.3 mg) in 60 mL of benzene is heated at reflux with a Dean-Stark trap for 18 hrs. The reaction mixture is diluted with 100 mL of ethyl acetate and successively washed with 100 mL each of aqueous saturated NaHCO3, H2O, and saturated brine. The organic phase is dried over anhydrous Na2SO4, filtered and concentrated in vacuo, affording 2-(4-Isopropoxy-2-methyl-5-nitro-phenyl)-2-methyl-[1,3]dioxolane as yellow crystals. MS (ES+): 282.2 (MH+).

Workup

  1. temperatureis heated
  2. temperatureat reflux with a Dean-Stark trap for 18 hrs
  3. washsuccessively washed with 100 mL each of aqueous saturated NaHCO3, H2O, and saturated brine
  4. dry with materialThe organic phase is dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-efc8ae16c03144acae5205024683f232
Source dataset
uspto-grants-2013_02
Patent number
US08377921B2

Reaction notes

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