Acetone → HCID 71578535, compound

HRID 1505023Notes

Reaction equation

HRID 1505023 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:8][CH:7]=1)=[O:5].CC(C)=O.[N:24]([O-:26])=[O:25].[Na+].CCCCCC>O>[N+:24]([CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:8][CH:7]=1)=[O:5])([O-:26])=[O:25]

Participants

6

Reactant 4

HCID 180AcetoneHCID 8058HexaneHCID 23668193Sodium Nitrite2×HCID 707007193-Chloro-1-(4-octylphenyl)propan-1-one

Product 1

HCID 71578535HCID 71578535, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

3-Chloro-1-(4-octylphenyl)propan-1-one (110 g) and acetone (1 L) are charged into a round bottom flask equipped with a condenser and guard tube and stirred. Sodium nitrite (271 g) is added and the mixture is slowly heated to 80° C. and maintained at that temperature for about 21 hours. The mass is cooled to 58° C., sodium nitrite (10 g) is added, and the mass is maintained at 78° C. for about 6 hours. The solvent is evaporated under reduced pressure. The compound obtained is diluted with water (250 mL) and extracted with ethyl acetate (2×500 mL). The combined organic layer is dried over anhydrous sodium sulphate (50 g) and concentrated under reduced pressure to give solid. Hexane (500 mL) is added and the mixture is cooled to −10° C. and stirred for 20 minutes. The formed solid is separated by filtration and washed with cold hexane (2×100 mL) to obtain the title compound as an off-white solid. Yield: 75 g.

Workup

  1. customequipped with a condenser and guard tube
  2. temperaturemaintained at that temperature for about 21 hours
  3. temperatureThe mass is cooled to 58° C.
  4. temperaturethe mass is maintained at 78° C. for about 6 hours
  5. customThe solvent is evaporated under reduced pressure
  6. customThe compound obtained
  7. extractionextracted with ethyl acetate (2×500 mL)
  8. dry with materialThe combined organic layer is dried over anhydrous sodium sulphate (50 g)
  9. concentrationconcentrated under reduced pressure
  10. customto give solid
  11. temperaturethe mixture is cooled to −10° C.
  12. stirringstirred for 20 minutes
  13. customThe formed solid is separated by filtration
  14. washwashed with cold hexane (2×100 mL)

Sources & evidence

ORD record
ord-67d67212d4ea4e34a763fbbaf25bf01b
Source dataset
uspto-grants-2015_12
Patent number
US09216943B2

Reaction notes

Loading…