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

HRID 1457598

反応式

HRID 1457598 の反応式
[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]

参加物

5

反応物 3

HCID 6332Ethyl BromideHCID 16043Tert-ButylhydroquinoneHCID 24758Sodium hydride

生成物 1

HCID 124236482-tert-Butyl-4-ethoxyphenol収率 22%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
-78 °C

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-0fcf3e76e20648fda250e06bb1d928a5
出典データセット
uspto-grants-1998_12
特許番号
US05849732

関連ノート

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