HCID 13799284, compound → HCID 13799285, compound

HRID 1086918Notes

Reaction equation

HRID 1086918 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9]C)[C:4]=1[CH2:11][CH2:12][C:13]([F:16])([F:15])[F:14]>C(Cl)Cl>[F:14][C:13]([F:15])([F:16])[CH2:12][CH2:11][C:4]1[C:5]([OH:9])=[CH:6][CH:7]=[CH:8][C:3]=1[OH:2]

Participants

3

Reactant 1

HCID 13799284HCID 13799284, compound

Product 1

HCID 13799285HCID 13799285, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

30.5 g (0.13 mole) of 1,3-dimethoxy-2-(3,3,3-trifluoropropyl)-benzene in 275 ml of methylene chloride are introduced into a 1.5 l sulfonating flask with a thermometer, bubble counter, dropping funnel with cooling jacket and argon connection and cooled to -75°. 340 ml of a precooled 1 molar solution of boron tribromide in methylene chloride are now added dropwise such that the reaction temperature does not rise above -70° (about 90 minutes). After subsequently stirring at room temperature for 6 hours, the red reaction solution is poured onto 800 ml of ice-water. The organic base is separated off, the aqueous phase is extracted again with ether and the combined organic phases are washed with brine, dried over magnesium sulfate and evaporated. 2-(3,3,3-Trifluoropropyl)-resorcinol is obtained in the form of red crystals of melting point 82°-84° (yield 100%).

Workup

  1. custombubble counter
  2. temperaturewith cooling jacket and argon connection
  3. temperaturecooled to -75°
  4. addition340 ml of a precooled 1 molar solution of boron tribromide in methylene chloride are now added dropwise such that the reaction temperature
  5. customdoes not rise above -70°
  6. custom(about 90 minutes)
  7. additionthe red reaction solution is poured onto 800 ml of ice-water
  8. customThe organic base is separated off
  9. extractionthe aqueous phase is extracted again with ether
  10. washthe combined organic phases are washed with brine
  11. dry with materialdried over magnesium sulfate
  12. customevaporated

Sources & evidence

ORD record
ord-eaaa8c1b714247ce935804f6a175d20b
Source dataset
uspto-grants-1991_07
Patent number
US05032606

Reaction notes

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