Phosphorus oxide (P4O10) → 3-Phenyl-7-propyl-1-benzofuran-6-ol

HRID 342772Notes

Reaction equation

HRID 342772 reaction equation
[CH2:1]([C:4]1[C:9]([O:10][CH2:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=O)=[CH:8][CH:7]=[CH:6][C:5]=1[OH:20])[CH2:2][CH3:3].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>OP(O)(O)=O.O.CCOCC>[C:14]1([C:12]2[C:8]3[CH:7]=[CH:6][C:5]([OH:20])=[C:4]([CH2:1][CH2:2][CH3:3])[C:9]=3[O:10][CH:11]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 543761242-Propyl-3-(2-phenyl-2-oxoethoxy)phenol

Product 1

HCID 154629143-Phenyl-7-propyl-1-benzofuran-6-ol

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherCatalystHCID 962WaterSolventHCID 1004Phosphoric AcidSolvent

Procedure

To a stirred suspension of 2-propyl-3-(2-phenyl-2-oxoethoxy)phenol (9.30 g) in o-phosphoric acid(85%) (93 mL) at room temperature was added over a 45 minutes period phosphorus pentoxide(46.50 g). During this period the reaction mixture was heated several times with a heat gun. After stirring the mixture for 30 minutes the reaction was checked by TLC (to take a little of sample with a capillary and dissolve sample in water and add several drops of ether; elution: 50% methylene chloride in hexane). The reaction mixture was heated again with heat gun if the reaction was not complete. The reaction mixture continued to be stirred for 20 minutes, then was poured into a beaker containing ice. The reaction flask was then rinsed with water and ether, and the washings were added to the beaker. The organic layer was separated, washed with water, dried over MgSO4, and concentrated. Column Chromatography (silica gel 60, 50% methylene chloride in hexane) gave the title compound.

Workup

  1. temperatureDuring this period the reaction mixture was heated several times with a heat gun
  2. washelution
  3. temperatureThe reaction mixture was heated again
  4. temperaturewith heat gun if the reaction
  5. stirringto be stirred for 20 minutes
  6. additionwas poured into a beaker
  7. additioncontaining ice
  8. washThe reaction flask was then rinsed with water and ether
  9. additionthe washings were added to the beaker
  10. customThe organic layer was separated
  11. washwashed with water
  12. dry with materialdried over MgSO4
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-142effbe0f39433290ee864692694e3e
Source dataset
uspto-grants-1999_01
Patent number
US05859051

Reaction notes

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