Ethanol → HCID 22158084, compound

HRID 1073243Notes

Reaction equation

HRID 1073243 reaction equation
[CH2:1]([OH:3])[CH3:2].S(=O)(=O)(O)[OH:5].[CH2:9]([O:12][C:13]1[CH:14]=[C:15]([CH2:19][C:20]#N)[CH:16]=[CH:17][CH:18]=1)[CH2:10][CH3:11]>O.CCOCC>[CH2:1]([O:3][C:20](=[O:5])[CH2:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([O:12][CH2:9][CH2:10][CH3:11])[CH:14]=1)[CH3:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 14711264HCID 14711264, compound

Product 1

HCID 22158084HCID 22158084, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A mixture of ethanol (3.9 g), water (0.2 g), conc.sulphuric acid (3.9 g) and 3-propyloxyphenylacetonitrile (3.5 g; 20 mmol) was heated under reflux during 6 hours. After cooling, ether (20 ml) and water (20 ml) were added and the mixture was stirred. The phases were separated and the ethereal extract washed with 10% potassium bicarbonate (2×20 ml), dried over Na2SO4, filtered and evaporated to dryness to give a pale tan oil.

Workup

  1. temperatureunder reflux during 6 hours
  2. temperatureAfter cooling
  3. customThe phases were separated
  4. extractionthe ethereal extract
  5. washwashed with 10% potassium bicarbonate (2×20 ml)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customto give a pale tan oil

Sources & evidence

ORD record
ord-27305afcded746caa68f54526b41a029
Source dataset
uspto-grants-1990_11
Patent number
US04968698

Reaction notes

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