O-Cresol → tert-Butyl-dimethyl-o-tolyloxy-silane

HRID 1927450Notes

Reaction equation

HRID 1927450 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.[C:14]1([CH3:21])[C:19]([OH:20])=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[C:4]([Si:1]([CH3:3])([CH3:2])[O:20][C:19]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:21])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 335O-CresolHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 11310617tert-Butyl-dimethyl-o-tolyloxy-silane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyldimethylsilyl chloride (83.6 g, 0.55 mol) and imidazole (78.69 g, 1.15 mol) were added to a solution of o-cresol (50 g, 0.46mol) in dry DMF (200 mL). The reaction mixture was stirred for 3 h, treated with a 5% aqueous NaHCO3 solution, extracted with petroleum ether and concentrated to obtain the title compound as an oil. Yield: 102 g, (100%); 1H NMR (CDCl3): δ 0.20 (s, 6H, 2CH3), 1.0 (s, 9H, 3CH3), 2.2 (s, 3H, CH3), 6.75 (d, 1H, Ar), 6.85 (q, 1H, Ar), 7.18 (q, 1H, Ar), 7.25 (d, 1H, Ar).

Workup

  1. extractionextracted with petroleum ether
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-01aeb2fe91ca49688989f01b43df96b8
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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