Water → Benzene, 1-(2,2-dimethoxyethoxy)-4-(1,1-dimethylethyl)-

HRID 35931

Reaction equation

HRID 35931 reaction equation
[H-].[Na+].[CH3:3][C:4]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)([CH3:6])[CH3:5].[CH3:14][O:15][CH:16]([O:19][CH3:20])[CH2:17]Br.O>CN(C)C=O>[CH3:6][C:4]([C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:17][CH:16]([O:19][CH3:20])[O:15][CH3:14])=[CH:11][CH:12]=1)([CH3:3])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 73934-tert-ButylphenolHCID 24758Sodium hydrideHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 3085718Benzene, 1-(2,2-dimethoxyethoxy)-4-(1,1-dimethylethyl)-Yield 94.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a mixture of 5.33 g (0.133 mol.) of sodium hydride (60%) and 200 ml of anhydrous N,N-dimethylformamide, there was added dropwise a solution of 20.00 g (0.133 mol.) of 4-(1,1-dimethylethyl)phenol in 50 ml of anhydrous N,N-dimethylformamide with stirring at a temperature of from 5° C. to 10° C. for 10 minutes. Then the reaction mixture was stirred at the same temperature for 30 minutes. To the above mixture, there was added dropwise 24.75 g (0.146 mol.) of bromoacetoaldehyde dimethylacetal in 50 ml of anhydrous N,N-dimethylformamide with stirring at the same temperature for 30 minutes. The reaction mixture was then stirred at room temperature for 20 hours. After the reaction was completed, the reaction mixture was poured into water and extracted with ethyl acetate. Then the residue was washed three times with a saturated aqueous solution of ammonium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to give 30.00 g of 2-[4-(1,1-dimethylethyl)phenoxy]-1,1-dimethoxyethane as a light-yellowish oily substance (nD22.8 1.4911).

Workup

  1. stirringThen the reaction mixture was stirred at the same temperature for 30 minutes
  2. stirringwith stirring at the same temperature for 30 minutes
  3. stirringThe reaction mixture was then stirred at room temperature for 20 hours
  4. extractionextracted with ethyl acetate
  5. washThen the residue was washed three times with a saturated aqueous solution of ammonium chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7d546d4e02db4bdd8ad5a755e1edb85c
Source dataset
uspto-grants-1995_05
Patent number
US05411979

Linked notes

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