Hydrochloric Acid → 1-(4-isopropoxyphenyl)propan-2-one

HRID 1731583Notes

Reaction equation

HRID 1731583 reaction equation
Cl.[CH:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[C:13]([N+]([O-])=O)[CH3:14])=[CH:8][CH:7]=1)([CH3:4])[CH3:3].[O:18]1CCCC1>[Fe]>[CH:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13](=[O:18])[CH3:14])=[CH:8][CH:7]=1)([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 541717311-(1-Methylethoxy)-4-(2-nitro-1-propen-1-yl)benzene

Product 1

HCID 9193321-(4-isopropoxyphenyl)propan-2-one

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Concentrated hydrochloric acid (90 ml) was added dropwise, over 45 minutes, to a stirred mixture of iron powder (17.5 g) and 1-(4-isopropoxyphenyl)-2-nitroprop1-ene (16.0 g) in tetrahydrofuran (50 ml) at reflux. The mixture was heated under reflux for a further hour, cooled, filtered through diatomaecous earth and the tetrahydrofuran removed under reduced pressure. The residue was diluted with water, extracted with diethyl ether, washed with brine, dried (magnesium sulphate), filtered and evaporated to dryness. Distillation of the residue gave the title compound, bp 120°-6°/1.5 mm.

Workup

  1. temperatureat reflux
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for a further hour
  4. temperaturecooled
  5. filtrationfiltered through diatomaecous earth
  6. customthe tetrahydrofuran removed under reduced pressure
  7. additionThe residue was diluted with water
  8. extractionextracted with diethyl ether
  9. washwashed with brine
  10. dry with materialdried (magnesium sulphate)
  11. filtrationfiltered
  12. customevaporated to dryness
  13. distillationDistillation of the residue

Sources & evidence

ORD record
ord-c20dbfec2e004b3f8259191b0db34ffc
Source dataset
uspto-grants-1986_11
Patent number
US04622342

Reaction notes

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