Tetrabutylammonium Fluoride → 2,6-Dimethyl-4-hydroxybenzaldehyde

HRID 1515000Notes

Reaction equation

HRID 1515000 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:14]=[C:13]([CH3:15])[C:10]([CH:11]=[O:12])=[C:9]([CH3:16])[CH:8]=1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:6][C:7]1[CH:8]=[C:9]([CH3:16])[C:10]([CH:11]=[O:12])=[C:13]([CH3:15])[CH:14]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 161282044-[(Tert-butyldimethylsilyl)oxy]-2,6-dimethylbenzaldehyde

Product 1

HCID 5910722,6-Dimethyl-4-hydroxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 4-(tert-butyldimethyl-silanyloxy)-2,6-dimethylbenzaldehyde (2.4 g, 9 mmol) in THF (10 mL) was added TBAF (10 mL of a 1.0 M solution in THF). After an hour at ambient temperature, the reaction mixture was quenched with water and the aqueous layer was extracted with EtOAc. The organic layer was washed with water, brine, dried with MgSO4 and filtered. The solvent was removed under reduced pressure to give 4-hydroxy-2,6-dimethylbenzaldehyde as a yellow oil.

Workup

  1. waitAfter an hour at ambient temperature
  2. customthe reaction mixture was quenched with water
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f65c9c577492461f98202656fddbd231
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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