Hydroquinone → 4-(Dec-9-enyloxy)phenol

HRID 634876

反応式

HRID 634876 の反応式
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[CH2:9](Br)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18].[OH-].[K+]>C(O)C.O>[CH2:18]([O:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH:10]=[CH2:9]

参加物

6

反応物 3

HCID 785HydroquinoneHCID 14797Potassium HydroxideHCID 54338410-Bromo-1-decene

生成物 1

HCID 158607774-(Dec-9-enyloxy)phenol収率 36.4%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

実験手順

Hydroquinone (37.65 g, 342 mmol) and dec-9-enyl bromide (25 g, 114 mmol) were dissolved in ethanol (150 ml) with warming under a nitrogen atmosphere. The solution was heated under reflux and a solution of potassium hydroxide (6.83 g, 121 mmol) in water (20 ml) was added dropwise over 1 h. The resulting suspension was heated under reflux (3 H) then poured on to water (500 ml) and extracted with ether (3×100 ml). The combined extracts were dried (MgSO4), evaporated in vacuo and the residue extracted with heptane (300 ml). On cooling, it afforded a first crop of the phenol (10.31 g). The remaining material was chromatographed (flash grade silica gel, petroleum ether 40-60° C./diethyl ether 3/2). 2 was isolated as white plates (Rf=0.57). Combined yield=15.61 g (55%). Mp=54° C.

後処理

  1. temperaturewith warming under a nitrogen atmosphere
  2. temperatureThe solution was heated
  3. temperatureunder reflux
  4. temperatureThe resulting suspension was heated
  5. temperatureunder reflux (3 H)
  6. extractionextracted with ether (3×100 ml)
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. customevaporated in vacuo
  9. extractionthe residue extracted with heptane (300 ml)
  10. temperatureOn cooling

出典と根拠

ORDレコード
ord-fb73047467264b8d946e2a5e2cc96875
出典データセット
uspto-grants-2001_02
特許番号
US06184322B2

関連ノート

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