Tetrabutylammonium Fluoride → Benzenemethanol, 3,5-dichloro-4-hydroxy-

HRID 2255603Notes

Reaction equation

HRID 2255603 reaction equation
[Si]([O:8][C:9]1[C:16]([Cl:17])=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][C:10]=1[Cl:18])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:17][C:16]1[CH:15]=[C:12]([CH:11]=[C:10]([Cl:18])[C:9]=1[OH:8])[CH2:13][OH:14]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 19385618HCID 19385618, compound

Product 1

HCID 176409Benzenemethanol, 3,5-dichloro-4-hydroxy-Yield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.83 g (5.96 mmol) of the product of Step B dissolved in 6 mL of THF was added 5.96 mL (5.96 mmol) of a 1M solution of tetra-n-butylammonium fluoride in THF and the reaction mixture was stirred at room temperature 30 minutes. The solution was then evaporated in vacuo and the residue was purified on a silica gel flash chromatography column eluted with 4% methanol/chloroform to afford 0.733 g (64%) of the title compound.

Workup

  1. customThe solution was then evaporated in vacuo
  2. customthe residue was purified on a silica gel flash chromatography column
  3. washeluted with 4% methanol/chloroform

Sources & evidence

ORD record
ord-d3f48595ff6a4b8490886526196f9970
Source dataset
uspto-grants-1993_08
Patent number
US05240938

Reaction notes

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