Methanol → 3'-(Hydroxymethyl)-2,6-dimethylbiphenyl-4-ol

HRID 15638ノート

反応式

HRID 15638 の反応式
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[O:16])[CH:10]=2)=[C:4]([CH3:17])[CH:3]=1.CO.[BH4-].[Na+]>O1CCCC1>[OH:16][CH2:15][C:11]1[CH:10]=[C:9]([C:5]2[C:4]([CH3:17])=[CH:3][C:2]([OH:1])=[CH:7][C:6]=2[CH3:8])[CH:14]=[CH:13][CH:12]=1

参加物

5

反応物 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 231116914'-Hydroxy-2',6'-dimethyl-[1,1'-biphenyl]-3-carbaldehyde

生成物 1

HCID 593425523'-(Hydroxymethyl)-2,6-dimethylbiphenyl-4-ol収率 93.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 4′-hydroxy-2′,6′-dimethylbiphenyl-3-carbaldehyde (6.95 q, 30.7 mmol) in a mixed solvent of methanol (30 mL) and tetrahydrofuran (60 mL) was ice-cooled, sodium borohydride (90%, 1.29 g, 30.7 mmol) was added, and the mixture was stirred for 20 hr under nitrogen atmosphere, during which the mixture was allowed to gradually warm to room temperature. The reaction mixture was concentrated under reduced pressure, the residue was treated with diluted hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crystals were recrystallized from heptane-ethyl acetate to give the title compound (6.56 g, yield 93%) as colorless crystals.

後処理

  1. temperaturecooled
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was treated with diluted hydrochloric acid
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained crystals were recrystallized from heptane-ethyl acetate

出典と根拠

ORDレコード
ord-68f156b4741b4933842ecb7e46216cf8
出典データセット
uspto-grants-2010_06
特許番号
US07732626B2

反応ノート

読み込み中…