4-Hydroxybenzaldehyde → 4-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehyde

HRID 330330Notes

Reaction equation

HRID 330330 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH3:10][C:11]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1.O>CN(C)C=O>[CH3:10][C:11]([Si:14]([CH3:16])([CH3:15])[O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 108791334-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehydeYield 96.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 10.4 grams (0.085 mole) of 4-hydroxybenzaldehyde in 36.5 mL of dimethylformamide was added 15.4 grams (0.102 mole) of (1,1-dimethylethyl)dimethylsilyl chloride and then 14.8 grams (0.218 mole) of imidazole. Upon completion of addition the reaction mixture was stirred under a nitrogen atmosphere at ambient temperature for three hours. The reaction mixture was poured into a separatory funnel, and water was added. The mixture was extracted with diethyl ether. The ether layer was washed in turn with one portion of aqueous 10% sodium hydroxide, one portion of aqueous 10% hydrochloric acid, one portion of water, and one portion of an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was dissolved in diethyl ether and was stirred for 20 minutes with decolorizing carbon and neutral alumina. The mixture was filtered through diatomaceous earth, and the filtrate was concentrated under reduced pressure to yield 19.4 grams of 4-[(1,1-dimethylethyl)dimethylsilyloxy]benzaldehyde. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. additionThe reaction mixture was poured into a separatory funnel
  3. extractionThe mixture was extracted with diethyl ether
  4. washThe ether layer was washed in turn with one portion of aqueous 10% sodium hydroxide, one portion of aqueous 10% hydrochloric acid, one portion of water, and one portion of an aqueous solution saturated with sodium chloride
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure to a residue
  8. dissolutionThe residue was dissolved in diethyl ether
  9. stirringwas stirred for 20 minutes with decolorizing carbon and neutral alumina
  10. filtrationThe mixture was filtered through diatomaceous earth
  11. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e7c83407d1404a53808b90272f26d922
Source dataset
uspto-grants-1990_01
Patent number
US04895871

Reaction notes

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