4-tert-Butylphenol → 4-(4-Tert-butylphenoxy)butyl acetate

HRID 5008

反応式

HRID 5008 の反応式
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].[O-]C1C=CC=CC=1.[C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28]Cl)(=[O:23])[CH3:22]>CN(C)C=O>[C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][O:13][C:10]1[CH:9]=[CH:8][C:7]([C:3]([CH3:6])([CH3:4])[CH3:5])=[CH:12][CH:11]=1)(=[O:23])[CH3:22]

参加物

6

反応物 4

HCID 73934-tert-ButylphenolHCID 233991-Butanol, 4-chloro-, 1-acetateHCID 24758Sodium hydrideHCID 119047Phenolate2 回

生成物 1

HCID 133137364-(4-Tert-butylphenoxy)butyl acetate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

To a stirred slurry of 1.6 g sodium hydride (as 50% dispersion in oil) in 50 ml dry dimethyl formamide was added, drop-wise, a solution of 5.0 g p-tert-butylphenol (33.3 mmoles) in 50 ml dry dimethyl formamide and the solution stirred under nitrogen until the phenoxide had totally formed. To the phenoxide was added a solution of 5.0 g 4-chlorobutyl acetate (33.3 mmoles) in 50 ml dry dimethyl formamide and the solution was stirred for fourteen hours. The reaction mixture was partitioned between water/toluene. The organic layer was removed, washed with water, then 1N sodium bicarbonate. The organic layer was removed, dried and evaporated to an orange oil, 5.6 g. The oil was chromatographed on 500 g, 90 to 200 mesh silica gel (CH2Cl2 eluent) yielding pure 4-(p-tert-butylphenoxy)-butyl acetate.

後処理

  1. customhad totally formed
  2. customThe reaction mixture was partitioned between water/toluene
  3. customThe organic layer was removed
  4. washwashed with water
  5. customThe organic layer was removed
  6. customdried
  7. customevaporated to an orange oil, 5.6 g
  8. customThe oil was chromatographed on 500 g, 90 to 200 mesh silica gel (CH2Cl2 eluent)

出典と根拠

ORDレコード
ord-cebef95bc8384043b4a84d71a6aab475
出典データセット
uspto-grants-1993_09
特許番号
US05242936

関連ノート

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