Hydrochloric Acid → Bis(3-isobutylphenyl)methanol

HRID 249143ノート

反応式

HRID 249143 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH:9]([CH3:11])[CH3:10])[CH:3]=1.[Mg].BrCCBr.[CH2:17]([C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=[O:25])[CH:18]([CH3:20])[CH3:19].Cl>O1CCCC1.II.C(OCC)(=O)C>[CH2:17]([C:21]1[CH:22]=[C:23]([CH:24]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH:9]([CH3:11])[CH3:10])[CH:3]=2)[OH:25])[CH:26]=[CH:27][CH:28]=1)[CH:18]([CH3:20])[CH3:19]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 78391,2-DibromoethaneHCID 5462224MagnesiumHCID 187549911-Bromo-3-isobutylbenzeneHCID 220441763-Isobutylbenzaldehyde

生成物 1

HCID 19024807Bis(3-isobutylphenyl)methanol収率 66.1%

試薬・触媒・溶媒 3

HCID 807Iodine触媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
25 °C

実験手順

A mixture of 1-bromo-3-isobutylbenzene (3.16 g), magnesium (1.08 g), 1,2-dibromoethane (2.78 g) and iodine (10 mg) in tetrahydrofuran (10 ml) was refluxed for 1.5 hours. The mixture was cooled to 25° C., and a solution of 3-isobutylbenzaldehyde (2.40 g) in tetrahydrofuran (10 ml) was added at 25° C. After stirred for 1 hour at the same temperature, the mixture was poured into a mixture of ethyl acetate and 1N hydrochloric acid. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. After evaporation of the solvent, the residue was chromatographed on silica gel (200 g) eluting with 5% ethyl acetate in hexane to give bis(3-isobutylphenyl)methanol (2.90 g) as a colorless oil.

後処理

  1. temperaturewas refluxed for 1.5 hours
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was chromatographed on silica gel (200 g)
  7. washeluting with 5% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-ece20f6a2d4d4ebbba9253f0cded847e
出典データセット
uspto-grants-1993_05
特許番号
US05212320

反応ノート

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