Sulfuric Acid → 6-[(2-chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl) oxy]-alpha-methyl-1H-benzotriazol-1-acetaldehyde

HRID 963661Notes

Reaction equation

HRID 963661 reaction equation
C[O:2][CH:3](OC)[CH:4]([CH3:27])[N:5]1[C:9]2[CH:10]=[C:11]([O:14][C:15]3[CH:20]=[C:19]([F:21])[C:18]([C:22]([F:25])([F:24])[F:23])=[C:17]([Cl:26])[CH:16]=3)[CH:12]=[CH:13][C:8]=2[N:7]=[N:6]1.OS(O)(=O)=O>C(O)(=O)C.O.C(Cl)Cl>[Cl:26][C:17]1[CH:16]=[C:15]([O:14][C:11]2[CH:12]=[CH:13][C:8]3[N:7]=[N:6][N:5]([CH:4]([CH3:27])[CH:3]=[O:2])[C:9]=3[CH:10]=2)[CH:20]=[C:19]([F:21])[C:18]=1[C:22]([F:25])([F:24])[F:23]

Participants

6

Reactant 2

HCID 1118Sulfuric AcidHCID 86747944HCID 86747944, compound

Product 1

HCID 867479486-[(2-chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl) oxy]-alpha-methyl-1H-benzotriazol-1-acetaldehyde

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 6-[(2-chloro-α,α,α,6-tetrafluoro-p-tolyl) oxy]-α-methyl-1H-benzotriazole-1-acetaldehyde dimethyl acetal (20 g, 0.046 mole) in acetic acid is treated with 47 ml of 2.5N H2SO4, heated for 12 hours at 70° C., cooled and diluted with water and methylene chloride. The phases are separated and the aqueous phase is extracted with methylene chloride. The combined organic phases are dried (MgSO4), filtered through a pad of Al2O3, and concentrated in vacuo to afford the title compound as a solid, mp 107°-108° C., characterized by elemental and NMR analyses.

Workup

  1. temperaturecooled
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted with methylene chloride
  4. dry with materialThe combined organic phases are dried (MgSO4)
  5. filtrationfiltered through a pad of Al2O3
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-81dd2c0583f94e4a9383e6b857dd4013
Source dataset
uspto-grants-1998_06
Patent number
US05763615

Reaction notes

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