Benzene → HCID 20337911, compound

HRID 1395680Notes

Reaction equation

HRID 1395680 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]([C:15]([OH:17])=[O:16])[CH2:12][C:11]=3[CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:19](O)[CH3:20].C1C=CC=CC=1.S(=O)(=O)(O)O>O>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]([C:15]([O:17][CH2:19][CH3:20])=[O:16])[CH2:12][C:11]=3[CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 702EthanolHCID 1118Sulfuric AcidHCID 20329640HCID 20329640, compound

Product 1

HCID 20337911HCID 20337911, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.5 g of 1D, 60 ml of ethanol, 20 ml of dry benzene and 2 ml of concentrated sulfuric acid was refluxed for seven hours, with removal of water as it formed. The resulting mixture was concentrated, and the residue dissolved in ether. The solution was washed with saturated sodium bicarbonate solution and water. The aqueous portion was extracted with ether. The combined organic layers were dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was distilled to give ethyl 2,3-dihydro-5-phenylbenzofuran-2-carboxylate (1E), as a colorless liquid, bp: 180°-181° C., 0.35 Torr.

Workup

  1. customformed
  2. concentrationThe resulting mixture was concentrated
  3. dissolutionthe residue dissolved in ether
  4. washThe solution was washed with saturated sodium bicarbonate solution and water
  5. extractionThe aqueous portion was extracted with ether
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. customthe solvent was evaporated under reduced pressure
  8. distillationThe residue was distilled

Sources & evidence

ORD record
ord-22961d1a368441a380e330c4e8350388
Source dataset
uspto-grants-1980_05
Patent number
US04205080

Reaction notes

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