4-叔丁基苯酚 → 4-(4-Tert-butylphenoxy)butyl acetate

HRID 544594

反应方程式

HRID 544594 反应方程式
[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]

参与物

6

反应物 4

HCID 73934-叔丁基苯酚HCID 233994-氯丁醇醋酸酯HCID 24758氢化钠HCID 119047Phenolate2 次

产物 1

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

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂3 次

实验过程

To a stirred slurry of 1.6 g sodium hydride (as 50% dispersion in oil) in 50 ml dry dimethyl formamide was added, dropwise, 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 1 N 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.

后处理

  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)

来源与证据

ORD记录
ord-68859b502a7640898737464c79dba6be
来源数据集
uspto-grants-1984_05
专利号
US04451474

关联笔记

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