1-Bromooctane → Benzophenone

HRID 2121313Notes

Reaction equation

HRID 2121313 reaction equation
O[C:2]1[CH:15]=[C:14](O)[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[OH-].[Na+].C(Br)CCCCCCC.[Na].OC1C(O)=C(C=CC=1)C(C1C=CC=CC=1)=O>C1(C)C=CC=CC=1.CC(CC(C)C)=O.CS(C)=O>[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])[C:3]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:2]=1

Participants

8

Reactant 4

HCID 81401-BromooctaneHCID 85722,4-DihydroxybenzophenoneHCID 14798Sodium Hydroxide2×HCID 69853432HCID 69853432, compound

Product 1

HCID 3102BenzophenoneYield 35%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolventHCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
40 °C

Procedure

2,4-dihydroxybenzophenone (5 g, 23 mmol) and polyethylenglycol (PEG 6000) (1 g) in toluene (25 ml) and NaOH 30% (6,26 g, 47 mmol) were loaded into a 100 ml three-necked flask. The solution was kept under reflux with Dien-Stark to remove water. The solution was cooled at 40° C. Dimethylsulfoxide (DMSO) (7 ml) and octylbromide (8 ml, 47 mmol) were added and the solution thus obtained was kept under reflux with Dien-Stark for 8 hours. NaOH 30% (30 ml) and methylisobutylketone (MIBK) (10 ml) were added. The aqueous phase containing the unreacted dihydroxybenzophenone sodium salt was separated from the solution. The organic phase was washed with water. The aqueous phase was reextracted with MIBK (10 ml). Both aqueous and organic phases were cloudy (the organic phase was filtered on silica). After removal of the solvent from the organic phase the crude product was dissolved in cool ethyl-acetate (9 ml) and methanol (65 ml) was added. The product crystallized at —5° C. The product was recrystallized from methanol at 30° C. cooling up to 10° C. (yield 35%; m.pt. 37,7-38,1° C.).

Workup

  1. temperatureunder reflux with Dien-Stark
  2. customto remove water
  3. customthe solution thus obtained
  4. temperatureunder reflux with Dien-Stark for 8 hours
  5. customwas separated from the solution
  6. washThe organic phase was washed with water
  7. filtrationwas filtered on silica)
  8. customAfter removal of the solvent from the organic phase the crude product
  9. dissolutionwas dissolved in cool ethyl-acetate (9 ml)
  10. additionmethanol (65 ml) was added
  11. customThe product crystallized at —5° C
  12. customThe product was recrystallized from methanol at 30° C.
  13. temperaturecooling up to 10° C. (yield 35%; m.pt. 37,7-38,1° C.)

Sources & evidence

ORD record
ord-4a29f3411e3b4ae3a0062adc171e713d
Source dataset
uspto-grants-2004_02
Patent number
US06696154B2

Reaction notes

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