Ethylene Glycol → HCID 21520276, compound

HRID 1282828Notes

Reaction equation

HRID 1282828 reaction equation
[C:1]([C:4]1[O:5][C:6]2[C:12]([CH2:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:7]=2[CH:8]=1)(=[O:3])[CH3:2].[CH2:15](O)[CH2:16][OH:17].O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:13]([C:12]1[C:6]2[O:5][C:4]([C:1]3([CH3:2])[O:17][CH2:16][CH2:15][O:3]3)=[CH:8][C:7]=2[CH:9]=[CH:10][CH:11]=1)[CH3:14]

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 962WaterHCID 124484571-(7-Ethyl-1-benzofuran-2-yl)ethan-1-one

Product 1

HCID 21520276HCID 21520276, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A stirred mixture of 50 g of 2-acetyl-7-ethylbenzofuran, 3.0 g of paratoluenesulphonic acid and 45.0 g of ethyleneglycol in 1200 ml of toluene was heated under reflux for 12 hours with azeotropic removal of water. The cooled solution was washed successively with dilute sodium hydroxide solution, water and brine and then dried over anhydrous sodium sulphate. The sodium sulphate was filtered off and the filtrate evaporated to dryness. The residual yellow oil was distilled under nitrogen to give 48.6 g of 7-ethyl-2-(2-methyl-1,3-dioxolan-2-yl)benzofuran of boiling point 86°-88°C/0.05 mm Hg.

Workup

  1. temperaturewas heated
  2. washThe cooled solution was washed successively with dilute sodium hydroxide solution, water and brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationThe sodium sulphate was filtered off
  5. customthe filtrate evaporated to dryness
  6. distillationThe residual yellow oil was distilled under nitrogen

Sources & evidence

ORD record
ord-3d961d26fdb64c97a62727b4d0e534cf
Source dataset
uspto-grants-1976_08
Patent number
US03972900

Reaction notes

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