Hydrochloric Acid → 1-(1-Benzofuran-2-yl)-1-(4-chlorophenyl)ethan-1-ol

HRID 364009Notes

Reaction equation

HRID 364009 reaction equation
[CH3:1]I.[Mg].[Cl:4][C:5]1[CH:21]=[CH:20][C:8]([C:9]([C:11]2[O:12][C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[CH:15]=2)=[O:10])=[CH:7][CH:6]=1.Cl>O1CCCC1>[O:12]1[C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[CH:15]=[C:11]1[C:9]([C:8]1[CH:20]=[CH:21][C:5]([Cl:4])=[CH:6][CH:7]=1)([OH:10])[CH3:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 838778Methanone, 2-benzofuranyl(4-chlorophenyl)-HCID 5462224Magnesium2×

Product 1

HCID 30678571-(1-Benzofuran-2-yl)-1-(4-chlorophenyl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

14.2 g of methyl iodide in 50 ml of tetrahydrofuran are dripped slowly onto 2.43 g of magnesium chips in about 30 ml of tetrahydrofuran. When all the magnesium has dissolved, 25.6 g of 2(p-chloro-benzoyl)benzofuran dissolved in 350 ml of tetrahydrofuran are added slowly. After the addition, the mixture is kept under reflux for 2 hours. It is cooled, poured into 500 g of crushed ice and 10 ml of concentrated HCl, then extracted with ethyl ether. The organic phase is washed with water, dried with anhydrous sodium sulphate, and evaporated to dryness, to leave a residue which crystallises from petroleum ether: M.P. 64°-66° C.

Workup

  1. additionare added slowly
  2. additionAfter the addition
  3. temperatureunder reflux for 2 hours
  4. temperatureIt is cooled
  5. extractionextracted with ethyl ether
  6. washThe organic phase is washed with water
  7. dry with materialdried with anhydrous sodium sulphate
  8. customevaporated to dryness
  9. customto leave a residue which
  10. customcrystallises from petroleum ether

Sources & evidence

ORD record
ord-8fd35cb86c324aae83229eb5576801dc
Source dataset
uspto-grants-1986_08
Patent number
US04604392

Reaction notes

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