Sulfuric Acid → HCID 18546485, compound

HRID 1267523Notes

Reaction equation

HRID 1267523 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:14]=NC(C)C)=[C:4]([CH3:19])[CH:3]=1.[OH:20]S(O)(=O)=O>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH:14]=[O:20])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[C:4]([CH3:19])[CH:3]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 18546514HCID 18546514, compound

Product 1

HCID 18546485HCID 18546485, compound

Procedure

A solution of 20.36 g (79.8 mmol) (4′-fluoro-2′-methyl-biphenyl-2-ylmethylene)-isopropyl-amine in 110 ml 4N H2SO4 was heated at reflux for 6 h. After cooling to RT, the solution was extracted twice with 150 ml CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/hexane 1:1) to give 4′-fluoro-2′-methyl-biphenyl-2-carbaldehyde as a pale yellow oil.

Workup

  1. temperatureat reflux for 6 h
  2. extractionthe solution was extracted twice with 150 ml CH2Cl2
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography (SiO2, CH2Cl2/hexane 1:1)

Sources & evidence

ORD record
ord-c1b300d12582458686b527652a0f4d40
Source dataset
uspto-grants-2003_04
Patent number
US06552088B2

Reaction notes

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