4-Hydroxybenzyl Alcohol → Phenol, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-

HRID 654216Notes

Reaction equation

HRID 654216 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1.CN(C)C=O>O>[O:1]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)[Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 1254-Hydroxybenzyl AlcoholHCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11230163Phenol, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.24 g (0.01 mole) of 4-hydroxymethylphenol, 1.8 g (0.012 mole) of tert-butyldimethylsilyl chloride, 1.7 g (0.025 mole) of imidazole and 3 ml of dimethylformamide was stirred under nitrogen at room temperature for 12 h. The reaction mixture was poured into water and extracted with three portions of ether. Ether extracts were combined and washed successively with water and saturated NaCl solution and then dried (Na2SO4). The ether solution was concentrated in-vacuo and the resultant crude product was purified by flash chromatography (silica; 10% ethyl acetate in hexanes) to give the title compound as a colorless oil.

Workup

  1. extractionextracted with three portions of ether
  2. washwashed successively with water and saturated NaCl solution
  3. dry with materialdried (Na2SO4)
  4. concentrationThe ether solution was concentrated in-vacuo
  5. customthe resultant crude product was purified by flash chromatography (silica; 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e065c27263aa4f32ba928fc186147cbb
Source dataset
uspto-grants-1992_07
Patent number
US05130335

Reaction notes

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