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

HRID 323426

Reaction equation

HRID 323426 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-da9b89e6766344bd8c9e243897e99ef9
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Linked notes

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