3,5-Dimethylphenol → HCID 66745641, compound

HRID 591848Notes

Reaction equation

HRID 591848 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>CN(C)C=O>[C:23]([Si:20]([O:19][CH2:18][CH2:17][O:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[CH:3]=1)([CH3:22])[CH3:21])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 79483,5-DimethylphenolHCID 11430Potassium CarbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 66745641HCID 66745641, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,5-dimethyl-phenol (3.000 g, 24.55 mmol) in N,N-dimethylformamide (120 mL) under nitrogen were added potassium carbonate (16.96 g, 122.7 mmol) and (2-bromoethoxy)-tert-butyldimethylsilane (7.90 mL, 36.8 mmol). The resulting slurry was heated at reflux for 20 hours; then, the solvent was removed under high vacuum. The residue was dissolved in ethyl acetate and the solution was backwashed with 0.2 N aqueous sodium hydroxide, water, and then brine, dried over sodium sulfate, and concentrated. The crude material (5.69 g) was purified by column chromatography (silica gel 230-400 mesh; methylene chloride as eluent) to give tert-butyl-[2-(3,5-dimethyl-phenoxy)-ethoxy]-dimethylsilane as light yellow oil. Yield: 3.72 g (47%).

Workup

  1. temperatureThe resulting slurry was heated
  2. temperatureat reflux for 20 hours
  3. customthen, the solvent was removed under high vacuum
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. dry with materialbrine, dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude material (5.69 g) was purified by column chromatography (silica gel 230-400 mesh; methylene chloride as eluent)

Sources & evidence

ORD record
ord-4130c481ec834644a757f973072fad97
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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