Ethylene Glycol → HCID 59764583, compound

HRID 1664663Notes

Reaction equation

HRID 1664663 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-6375120ec689402990f1cf64a8e52f81
Source dataset
uspto-grants-2011_10
Patent number
US08039479B2

Reaction notes

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