Hydrochloric Acid → 3-Nitro-1-phenylpropan-1-one

HRID 1028873Notes

Reaction equation

HRID 1028873 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[N+:5]([CH2:8][CH2:9][C:10](Cl)=[O:11])([O-:7])=[O:6].C([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)CCCCCCC.Cl>C(Cl)Cl>[N+:5]([CH2:8][CH2:9][C:10]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:11])([O-:7])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 16607OctylbenzeneHCID 6451240Aluminum(III) ChlorideHCID 126886603-Nitropropanoyl chloride

Product 1

HCID 5694913-Nitro-1-phenylpropan-1-oneYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

AlCl3 (12.0 g, 89.0 mmol) was added to 15 ml of methylene chloride and cooled to 0-5° C., following by addition of 3-nitropropanoyl chloride (11 g, 80 mmol). Octylbenzene (17.10 g, 89.0 mmol) in 40 ml of CH2Cl2 was dropwise added and the solution was stirred at room temperature under TLC monitoring. After reaction completion, the mixture was poured onto ice, acidified by addition of 2 M HCl to pH 2, and extracted with CH2Cl2. The combined organic extracts were washed again with 2 M HCl and water, dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to yield a solid that was recrystallized (hexanes) to give 3-nitro-1-phenylpropan-1-one (76%); mp 59-62° C., ESIMS 292 [M+H]+.

Workup

  1. customAfter reaction completion
  2. additionthe mixture was poured onto ice
  3. extractionextracted with CH2Cl2
  4. washThe combined organic extracts were washed again with 2 M HCl and water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customto yield a solid
  9. customthat was recrystallized (hexanes)

Sources & evidence

ORD record
ord-45ec242ba9af4d9780897ec92f10dac4
Source dataset
uspto-grants-2014_05
Patent number
US08735627B2

Reaction notes

Loading…