Ethanol → HCID 22929815, compound

HRID 1295953Notes

Reaction equation

HRID 1295953 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16](=[O:18])[CH3:17])[CH:8]=[C:9]([N+:13]([O-])=O)[C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].C(O)C.O>[Fe].C(OCC)(=O)C>[NH2:13][C:9]1[CH:8]=[C:7]([C:16](=[O:18])[CH3:17])[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]=1[O:11][CH3:12]

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 589100541-(3-tert-Butyl-4-methoxy-5-nitrophenyl)ethan-1-one

Product 1

HCID 22929815HCID 22929815, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Iron powder (365 g) was added to a mixture of 1-[3-(tert-butyl)-4-methoxy-5-nitrophenyl]-1-ethanone (850 g), ammonium chloride (723 g), ethanol (4 l) and water (1 l) at 70° C. to 80° C. over a period of 1 hour. The reaction mixture was cooled to room temperature and then poured into a mixture of ice water and ethyl acetate and filtered through celite. The organic layer of the mother liquor was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the resulting crystals were filtered off to yield the title compound (362 g) as white crystals.

Workup

  1. filtrationfiltered through celite
  2. washThe organic layer of the mother liquor was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. filtrationthe resulting crystals were filtered off

Sources & evidence

ORD record
ord-33a2a1170a504d928d28cf91ab1e61c5
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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