Ethyl Bromide → 2-tert-Butyl-4-ethoxyphenol

HRID 1457598

Reaction equation

HRID 1457598 reaction equation
[C:1]([C:5]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=1[OH:7])([CH3:4])([CH3:3])[CH3:2].[CH2:13](Br)[CH3:14].[H-].[Na+]>CN(C)C=O>[CH2:13]([O:12][C:10]1[CH:9]=[CH:8][C:6]([OH:7])=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:11]=1)[CH3:14]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 16043Tert-ButylhydroquinoneHCID 24758Sodium hydride

Product 1

HCID 124236482-tert-Butyl-4-ethoxyphenolYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-78 °C

Procedure

A mixture of 19.85 g of tert-butylhydroquinone, 10.7 ml of ethyl bromide and 200 ml of dimethylformamide (DMF) was cooled to -78° C., and 4.82 g of 62.5% sodium hydride was added to the mixture. The temperature of the mixture was raised to 0° C., and the mixture was further stirred under ice-cooling for 30 minutes. The reaction mixture was poured into ice water, and the mixture was extracted with ethyl acetate. The extract was washed and dried, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=10:1), and recrystallized from hexane to give 5.045 g of 4-ethoxy-2-tert-butylphenol (yield: 22%, melting point: 96°-98° C.).

Workup

  1. temperatureThe temperature of the mixture was raised to 0° C.
  2. temperaturecooling for 30 minutes
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed
  5. customdried
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=10:1)
  8. customrecrystallized from hexane

Sources & evidence

ORD record
ord-0fcf3e76e20648fda250e06bb1d928a5
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Linked notes

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