Sulfuric Acid → HCID 23344098, compound

HRID 916829Notes

Reaction equation

HRID 916829 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]#N.[OH:14]S(O)(=O)=O.[C:19](=O)([O-])[O-:20].[Na+].[Na+]>CO>[OH:1][CH2:2][CH2:3][O:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]([O:20][CH3:19])=[O:14]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 284140323-[(2-Hydroxyethoxy)methyl]benzonitrile

Product 1

HCID 23344098HCID 23344098, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-[(2-hydroxyethoxy)methyl]benzonitrile (1 g) in MeOH (20 ml) was treated with conc. H2SO4 (10 ml) at 0° C. The solution was then allowed to warm to room temperature before heating at reflux for 10 h. Aqueous sodium carbonate was added to neutralise the cooled solution before extracting with EtOAc. The combined organic layers were then washed with water, dried (MgSO4) and concentrated in vacuo. The residue was then purified by chromatography (Biotage, 90 g) eluting with 40°C.-60° C. petroleum ether-EtOAc (3:2) to give the title compound (650 mg). LCMS RT=2.33 min.

Workup

  1. temperaturebefore heating
  2. temperatureat reflux for 10 h
  3. extractionbefore extracting with EtOAc
  4. washThe combined organic layers were then washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was then purified by chromatography (Biotage, 90 g)
  8. washeluting with 40°C.-60° C. petroleum ether-EtOAc (3:2)

Sources & evidence

ORD record
ord-d181df1061e84f148cd922d7ca34c8b2
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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