Methanol → beta,beta-Dimethylbenzeneethanol

HRID 74012

反応式

HRID 74012 の反応式
[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:6])[C:3](O)=[O:4].CSC.B.CO.O>C1COCC1>[CH3:6][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:1])[CH2:3][OH:4]

参加物

6

反応物 4

HCID 887MethanolHCID 962WaterHCID 132222-Phenylisobutyric acidHCID 12423031(Dimethyl sulfide)trihydroboron

生成物 1

HCID 219535beta,beta-Dimethylbenzeneethanol収率 93.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-methyl-2-phenyl-propionic acid (82 g, 0.5 mol) in THF (200 mL) was added dropwise borane-dimethyl sulfide (2M, 100 mL) at 0-5° C. The mixture was stirred at this temperature for 30 min and then heated at reflux for 1 h. After cooling, methanol (150 mL) and water (50 mL) were added. The mixture was extracted with EtOAc (100 mL×3), and the combined organic layers were washed with water and brine, dried over Na2SO4 and concentrated to give 2-methyl-2-phenyl-propan-1-ol as an oil (70 g, 77%).

後処理

  1. temperatureheated
  2. temperatureat reflux for 1 h
  3. temperatureAfter cooling
  4. extractionThe mixture was extracted with EtOAc (100 mL×3)
  5. washthe combined organic layers were washed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-b19017f1db594f9c818466d35370075d
出典データセット
uspto-grants-2014_09
特許番号
US08829204B2

関連ノート

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