1,4-Dibromobutane → 6-(4-Bromobutyloxy)indanone

HRID 253688Notes

Reaction equation

HRID 253688 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:18][CH2:19][CH2:20][CH2:21][CH2:22]Br>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 70206596-Hydroxy-1-indanone

Product 1

HCID 115509406-(4-Bromobutyloxy)indanoneYield 65.4%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 180AcetoneSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 6-hydroxyindan-1-one (100 gm, 0.675 mol), potassium carbonate (96 gm, 0.695 mol), 1,4-dibromo butane (365 gm, 1.69 mol) and tetrabutyl ammonium bromide in acetone was introduced in to a three necked round bottomed flask filtered with a water condenser and a mechanical stirrer. The mixture was brought to a temperature 65° C. and maintained at 65° C. for nine hours and then distilled off solvent, diluted with water (400 ml). The aqueous layer was extracted with ethyl acetate, and the extract was washed with water, dried and evaporated in the rotavapour under reduced pressure to get a residue which on crystallization from isopropyl ether gave 125 gm of 6-(4-bromo butoxy)-indan-1-one of the formula 3

Workup

  1. additionwas introduced in to a three necked round bottomed flask
  2. filtrationfiltered with a water condenser and a mechanical stirrer
  3. customwas brought to a temperature 65° C.
  4. distillationdistilled off solvent
  5. additiondiluted with water (400 ml)
  6. extractionThe aqueous layer was extracted with ethyl acetate
  7. washthe extract was washed with water
  8. customdried
  9. customevaporated in the rotavapour under reduced pressure
  10. customto get a residue which
  11. customon crystallization from isopropyl ether

Sources & evidence

ORD record
ord-714eff7f063b4ac3ad5ae949c4eac40d
Source dataset
uspto-grants-2011_01
Patent number
US07872132B2

Reaction notes

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