Ethylene Glycol → HCID 14547485, compound

HRID 2232360Notes

Reaction equation

HRID 2232360 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[CH:11]=[CH:10][S:9][C:8]=2[CH:12]=1)(=[O:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:24](O)[CH2:25][OH:26].O>C1(C)C=CC=CC=1>[CH3:2][C:1]1([C:4]2[CH:5]=[CH:6][C:7]3[CH:11]=[CH:10][S:9][C:8]=3[CH:12]=2)[O:26][CH2:25][CH2:24][O:3]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 14547484HCID 14547484, compound

Product 1

HCID 14547485HCID 14547485, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 6-acetyl benzo[b]thiophene (10.57 g, 60 mmole), p-toluenesulfonic acid (1.65 g) and ethylene glycol (33 ml) was heated to reflux in toluene (250 ml) for 2 hours with the continuous removal of H2O using a Dean-Stark trap. The reaction mixture was allowed to cool to room temperature. Then extracted with 20% saturated NaHCO3 (150 ml) and H2O (2×150 ml). After drying over Na2SO4, the solvent was evaporated in vacuo and the residue was crystallized from hexanes (50 ml) yielding 9.66 g (73%) of product.

Workup

  1. temperaturewas heated
  2. extractionThen extracted with 20% saturated NaHCO3 (150 ml) and H2O (2×150 ml)
  3. dry with materialAfter drying over Na2SO4
  4. customthe solvent was evaporated in vacuo
  5. customthe residue was crystallized from hexanes (50 ml)

Sources & evidence

ORD record
ord-97a784b5264a49c5a7c1a37adef928df
Source dataset
uspto-grants-1988_11
Patent number
US04788192

Reaction notes

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