Tetrabutylammonium Fluoride → 4-Hydroxy-2-isopropylbenzaldehyde

HRID 278797Notes

Reaction equation

HRID 278797 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[C:9]([CH:15]([CH3:17])[CH3:16])[CH:8]=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[C:9]([CH:15]([CH3:17])[CH3:16])[CH:8]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 225689004-(Tert-butyl-dimethyl-silanyloxy)-2-isopropyl-benzaldehyde2×

Product 1

HCID 225689144-Hydroxy-2-isopropylbenzaldehydeYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-(tert-butyl-dimethyl-silanyloxy)-2-isopropyl-benzaldehyde (Intermediate 146, 880.0 mg, 3.17 mmols) in 6 mL THF at 0° C. was added tetrabutylammonium fluoride (1.66 g, 6.33 mmols; 6.3 mL of a 1M solution in THF). The pale-yellow solution was stirred for 30 minutes and quenched by the addition of ice cold H2O. The mixture was extracted with Et2O and the combined organic layers were washed with H2O and saturated aqueous NaCl before being dried (Na2SO4) and concentrated under reduced pressure. Column chromatography (20% EtOAc-hexanes) afforded 500.0 mg (96%) of the title compound as a colorless solid.

Workup

  1. customquenched by the addition of ice cold H2O
  2. extractionThe mixture was extracted with Et2O
  3. washthe combined organic layers were washed with H2O and saturated aqueous NaCl
  4. dry with materialbefore being dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-998cc26cee8a4486a3eb2a776b050b26
Source dataset
uspto-grants-2002_03
Patent number
US06359135B1

Reaction notes

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