1-Bromo-3-chloropropane → HCID 10934655, compound

HRID 1810603Notes

Reaction equation

HRID 1810603 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH2:25][Cl:26]>CC(=O)CC>[Cl:26][CH2:25][CH2:24][CH2:23][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 143474-Hydroxybenzophenone

Product 1

HCID 10934655HCID 10934655, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

253.7 g (1.27 mol) 4-hydroxybenzophenone was dissolved in 2.56 L 2-butanone. 884.5 g (6.3 mol) potassium carbonate and 201.5 g (1.27 mol) 1-bromo-3-chloro-propane were added. The mixture was refluxed for 16 hours. The mixture was allowed to cool down to room temperature and the inorganic salts were removed by filtration. The solvent was removed under reduced pressure. The residue was treated with 250 mL acetone and 600 mL isopropyl acetate. The residue partially solidified. The solvent was removed and the residue was treated with 1.5 L water. The crude 4-(3-chloropropoxy)benzophenone crystallized from the medium, was isolated by filtration and dried. 228 g of the crude 4-(3-chloropropoxy)benzophenone was isolated.

Workup

  1. temperatureThe mixture was refluxed for 16 hours
  2. customthe inorganic salts were removed by filtration
  3. customThe solvent was removed under reduced pressure
  4. additionThe residue was treated with 250 mL acetone and 600 mL isopropyl acetate
  5. customThe solvent was removed
  6. additionthe residue was treated with 1.5 L water
  7. customThe crude 4-(3-chloropropoxy)benzophenone crystallized from the medium
  8. customwas isolated by filtration
  9. customdried

Sources & evidence

ORD record
ord-fba3d00d0cd7457697756d904fab7431
Source dataset
uspto-grants-2013_01
Patent number
US08362101B2

Reaction notes

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