Ethylene Glycol → 2-(5-tert-Butyl-2-methoxy-3-nitro-phenyl)-[1,3]dioxolane

HRID 1787454Notes

Reaction equation

HRID 1787454 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N+:15]([O-:17])=[O:16])[C:8]([O:13][CH3:14])=[C:9]([CH:12]=1)[CH:10]=[O:11])([CH3:4])([CH3:3])[CH3:2].[CH2:18](O)[CH2:19][OH:20]>C1C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]([N+:15]([O-:17])=[O:16])[C:8]([O:13][CH3:14])=[C:9]([CH:10]2[O:20][CH2:19][CH2:18][O:11]2)[CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 584939905-Tert-butyl-2-methoxy-3-nitrobenzaldehyde

Product 1

HCID 670199092-(5-tert-Butyl-2-methoxy-3-nitro-phenyl)-[1,3]dioxolane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1.0 g (4.2 mmol) of 5-tert-Butyl-2-methoxy-3-nitro-benzaldehyde, 1.18 mL of ethylene glycol, and 0.4 g of pTSA hydrate in 50 mL of benzene was refluxed for 24 h under Dean-Stark conditions. The benzene was evaporated and the resultant oil was redissolved in EtOAc. The organic layer was washed with water, sat'd NaHCO3, and brine. The extract was dried over MgSO4, filtered, and concentrated. Chromatography (10% EtOAc in hexanes) provided 1.0 g of 2-(5-tert-Butyl-2-methoxy-3-nitro-phenyl)-[1,3]dioxolane as a light yellow oil.

Workup

  1. customThe benzene was evaporated
  2. dissolutionthe resultant oil was redissolved in EtOAc
  3. washThe organic layer was washed with water
  4. dry with materialThe extract was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5eed70f3da81445780924b9cad065252
Source dataset
uspto-grants-2009_03
Patent number
US07511042B2

Reaction notes

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