Benzenesulfonic Acid → HCID 21520275, compound

HRID 1282830Notes

Reaction equation

HRID 1282830 reaction equation
[C:1]([O:4][CH:5]([C:7]1[C:15]2[O:14][C:13]([C:16]3([CH3:21])OCC[O:17]3)=[CH:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)[CH3:6])(=[O:3])[CH3:2].C1(S(O)(=O)=O)C=CC=CC=1>CC(C)=O>[C:16]([C:13]1[O:14][C:15]2[C:7]([CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH3:6])=[CH:8][CH:9]=[CH:10][C:11]=2[CH:12]=1)(=[O:17])[CH3:21]

Participants

4

Reactant 2

HCID 7371Benzenesulfonic AcidHCID 21520273HCID 21520273, compound

Product 1

HCID 21520275HCID 21520275, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ca 30 g of crude 7-(1'-acetoxyethyl)-2-(2-methyl-1,3-dioxolan-2-yl) benzofuran were dissolved in 200 ml of acetone and 2 ml of a 33% aqueous solution of benzenesulphonic acid were added to the solution obtained. The resulting solution was heated under reflux for 3 hours, then cooled and evaporated to dryness under reduced pressure. The residual oil was dissolved in diethyl ether and the solution washed with water and with brine and then dried over anhydrous sodium sulphate. The sodium sulphate was then filtered off and the filtrate evaporated to dryness under reduced pressure. The product was purified by column chromatography on silica gel followed by crystallization from cyclohexane to give 2-acetyl-7-(1'-acetoxyethyl)benzofuran in the form of a cream crystalline solid of melting point 82°-83°C.

Workup

  1. customobtained
  2. temperatureThe resulting solution was heated
  3. temperatureunder reflux for 3 hours
  4. temperaturecooled
  5. customevaporated to dryness under reduced pressure
  6. dissolutionThe residual oil was dissolved in diethyl ether
  7. washthe solution washed with water and with brine
  8. dry with materialdried over anhydrous sodium sulphate
  9. filtrationThe sodium sulphate was then filtered off
  10. customthe filtrate evaporated to dryness under reduced pressure
  11. customThe product was purified by column chromatography on silica gel
  12. customfollowed by crystallization from cyclohexane

Sources & evidence

ORD record
ord-c77eb749108742c8aa45e66b9eaba556
Source dataset
uspto-grants-1976_08
Patent number
US03972900

Reaction notes

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