Diethyl Ether → (1,1'-Biphenyl)-2,2'-dimethanol

HRID 132731

反応式

HRID 132731 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)C.[C:12]1([C:23]2[C:24]([C:29](OCC)=[O:30])=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:13]([C:18](OCC)=[O:19])=[CH:14][CH:15]=[CH:16][CH:17]=1>O>[C:23]1([C:12]2[C:13]([CH2:18][OH:19])=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:24]([CH2:29][OH:30])=[CH:25][CH:26]=[CH:27][CH:28]=1

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 13793399Diethyl diphenateHCID 21226445Aluminium lithium hydride2 回

生成物 1

HCID 243265(1,1'-Biphenyl)-2,2'-dimethanol収率 75%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To 3 g LiAlH4 was added 100 ml anhydrous ethyl ether. While cooling with ice-bath and stirring intensely, 0.05 mol diethyl 2,2′-biphenyldicarboxylate was slowly added dropwise. The reaction mixture was heated refluxing for 5 hours, then cooled. Excess LiAlH4 was decomposed with water. The mixture was filtered, and the filtrate was extracted with ethyl ether. The extract was dried over anhydrous sodium sulfate. The solvent was removed. Column chromatography gave 2,2′-biphenyldimethanol as a white solid, the yield was 75%, and m.p. was 98-103° C. IR spectrum had a strong absorption peak at 3400 cm−1, and had no absorption peak at about 1700 cm−1. This demonstrated that the reduction reaction was carried out completely.

後処理

  1. temperatureWhile cooling with ice-bath
  2. temperatureThe reaction mixture was heated
  3. temperaturerefluxing for 5 hours
  4. temperaturecooled
  5. filtrationThe mixture was filtered
  6. extractionthe filtrate was extracted with ethyl ether
  7. dry with materialThe extract was dried over anhydrous sodium sulfate
  8. customThe solvent was removed

出典と根拠

ORDレコード
ord-ab470297c5914f69bc4375f8fe401930
出典データセット
uspto-grants-2008_06
特許番号
US07388061B2

関連ノート

読み込み中…