Hydrochloric Acid → 1-[3-(Tert-butyl)-4-hydroxy-5-nitrophenyl]-1-ethanone

HRID 1295952Notes

Reaction equation

HRID 1295952 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:12](=[O:14])[CH3:13])[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[N+:15]([O-])([OH:17])=[O:16].C(OC(=O)C)(=O)C.Cl>C(OCC)C.C(Cl)Cl.O>[C:1]([C:5]1[CH:6]=[C:7]([C:12](=[O:14])[CH3:13])[CH:8]=[C:9]([N+:15]([O-:17])=[O:16])[C:10]=1[OH:11])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 137241451-(3-Tert-butyl-4-hydroxyphenyl)ethanone

Product 1

HCID 229297281-[3-(Tert-butyl)-4-hydroxy-5-nitrophenyl]-1-ethanoneYield 98%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

1-[3-(tert-Butyl)-4-hydroxyphenyl]-1-ethanone (739 g) was added to a mixture of 69% nitric acid (354 g), water (1 l) and methylene chloride (2 l) at 10° C. to 15° C. while stirring. After then adding diethyl ether (3 l) and acetic anhydride (28 ml), 5 N hydrochloric acid was further added at 10° C. to 15° C. The temperature of the reaction mixture was raised to room temperature over a period of 1.5 hours, and the mixture was then poured into ice water. The mixture was extracted with diethyl ether, and the organic layer was washed with brine and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to yield the title compound (894 g) as a yellow oil.

Workup

  1. extractionThe mixture was extracted with diethyl ether
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-bc7245931abb4cac8bf7473361ab7406
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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