Sulfuric Acid → 2-Methoxy-5-(trifluoromethoxy)benzaldehyde

HRID 1584471

Reaction equation

HRID 1584471 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]([F:13])([F:12])[F:11])=[CH:5][CH:4]=1.FC(F)(F)[C:16](O)=[O:17].C1N2CN3CN(C2)CN1C3.S(=O)(=O)(O)O>C(OCC)(=O)C.CCCCCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]([F:11])([F:12])[F:13])=[CH:5][C:4]=1[CH:16]=[O:17]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 27249731-Methoxy-4-(trifluoromethoxy)benzene

Product 1

HCID 27833642-Methoxy-5-(trifluoromethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
60 °C

Procedure

Combine 2-methoxy-5-trifluoromethoxybenzene (1.0 g, 5.2 mmol) and trifluoroacetic acid (200 mL). Add slowly portionwise hexamethylenetetraamine (26 g, 185.7 mmol). Heat at 60° C. After 24 hours, cool to ambient temperature and pour the reaction mixture into a 2 M aqueous solution of sulfuric acid (500 mL). Cool and extract ten times with diethyl ether. Dry the combined organic layers over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 1/4 ethyl acetate/hexane to give 2-methoxy-5-trifluoromethoxybenzaldehyde.

Workup

  1. temperaturecool to ambient temperature
  2. temperatureCool
  3. extractionextract ten times with diethyl ether
  4. dry with materialDry the combined organic layers over Na2SO4
  5. filtrationfilter
  6. customevaporate in vacuo
  7. customto give a residue

Sources & evidence

ORD record
ord-0b411b3408fb49bd99fca1fbc7f320ca
Source dataset
uspto-grants-1999_08
Patent number
US05932571

Linked notes

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