Hydrochloric Acid → 4-Acetyl-4'-hydroxy-2-nitro biphenyl

HRID 1460890Notes

Reaction equation

HRID 1460890 reaction equation
[Al](Br)(Br)Br.[C:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=2)=[C:10]([N+:22]([O-:24])=[O:23])[CH:9]=1)(=[O:7])[CH3:6].CCCCCC.C(OCC)(=O)C.Cl>C1C=CC=CC=1>[C:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=2)=[C:10]([N+:22]([O-:24])=[O:23])[CH:9]=1)(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24409Aluminum bromideHCID 189566161-(4'-Methoxy-2-nitro-[1,1'-biphenyl]-4-yl)ethanoneHCID 21226206Ethyl acetate hexane

Product 1

HCID 189566144-Acetyl-4'-hydroxy-2-nitro biphenyl

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred solution of AlBr3 (12.6 g, 47.4 mmole) in benzene (45 mL) is added dropwise under nitrogen a solution of the methylether (5 g, 18.45 mmole) of Step A in benzene (12 mL) over 30 minutes. The resulting solution is stirred at room temperature for 3.5 hours. (TLC, 8:2 hexane-ethyl acetate). The mixture is cooled in an ice bath and the complex is decomposed by the dropwise addition of 6N-HCl (ca. 37 mL). The organic layer is separated and the aqueous phase is reextracted with ether (3×). The combined extracts are concentrated to a small volume and extracted again with 2.5N-NaOH (2×50 mL+1×10 mL). The basic extracts are cooled and acidified with concentrated HCl (to pH 2). The solid is collected and dried (4.27 g, 90%). It is used in the next step without further purification.

Workup

  1. temperatureThe mixture is cooled in an ice bath
  2. customThe organic layer is separated
  3. concentrationThe combined extracts are concentrated to a small volume
  4. extractionextracted again with 2.5N-NaOH (2×50 mL+1×10 mL)
  5. temperatureThe basic extracts are cooled
  6. customThe solid is collected
  7. customdried (4.27 g, 90%)
  8. customIt is used in the next step without further purification

Sources & evidence

ORD record
ord-90d0ecb6658e475bb63acbcb220435d1
Source dataset
uspto-grants-1991_12
Patent number
US05071988

Reaction notes

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