3-Hydroxybenzaldehyde → 3-(t-Butyldimethylsilyloxy)benzaldehyde

HRID 1460110Notes

Reaction equation

HRID 1460110 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[C:10]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])([CH3:12])[CH3:11].N1C=CN=C1.O>CN(C)C=O>[Si:14]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 112071113-(t-Butyldimethylsilyloxy)benzaldehydeYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-hydroxy benzaldehyde (183.6 g, 1.50 mol), tert-butylchlorodimethylsilane (227.6 g, 1.50 mol), and imidazole (255.4 g, 3.75 mol) in 700 mL of dimethylformamide was stirred overnight at room temperature. The reaction solution was poured into 1700 mL of water and extracted with three 350 mL portions of diethyl ether. The combined ether extracts were washed with two 350 mL portions of 1.0M sodium hydroxide, 350 ml of water, and 350 mL of saturated aqueous sodium chloride. The ether solution was dried over sodium sulfate and the solvent removed to give 268 g (76%) of 3-(tert-butyldimethylsilyloxy)benzaldehyde as a yellow oil.

Workup

  1. extractionextracted with three 350 mL portions of diethyl ether
  2. washThe combined ether extracts were washed with two 350 mL portions of 1.0M sodium hydroxide, 350 ml of water, and 350 mL of saturated aqueous sodium chloride
  3. dry with materialThe ether solution was dried over sodium sulfate
  4. customthe solvent removed

Sources & evidence

ORD record
ord-cd2e321a8ae04e2c96019f188ff5b59b
Source dataset
uspto-grants-1998_12
Patent number
US05854249

Reaction notes

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