3-Hydroxybenzaldehyde → 3-(1-Hydroxy-2-nitroethyl)-phenol

HRID 20344

反応式

HRID 20344 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[N+:10]([CH3:13])([O-:12])=[O:11].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[OH:6][CH:5]([C:4]1[CH:3]=[C:2]([OH:1])[CH:9]=[CH:8][CH:7]=1)[CH2:13][N+:10]([O-:12])=[O:11]

参加物

6

反応物 3

HCID 1013-HydroxybenzaldehydeHCID 6375NitromethaneHCID 2724141Tetrabutylammonium Fluoride

生成物 1

HCID 444780213-(1-Hydroxy-2-nitroethyl)-phenol収率 90%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Dissolve 3-hydroxybenzaldehyde (18.4 g, 15.07 mmol) in tetrahydrofuran (100 mL). Add nitromethane ((42 mL, 780 mmol), cool in an ice bath and add tetrabutylammonium fluoride (151 mL, 151 mmol, 1.0 M in tetrahydrofuran). Stir for 2 hours, dilute with ethyl acetate (200 mL), wash with water (3×500 mL) and saturated aqueous sodium chloride (200 mL). Extract the aqueous washes with diethyl ether (3×), wash with saturated aqueous sodium chloride, dry (magnesium sulfate), filter through a pad of silica gel, and concentrate. Suspend the residue in hot dichloromethane with 5% ethyl acetate, cool and filter solid. Purify filtrate using silica gel chromatography, eluting with 5:95 ethyl acetate:dichloromethane. Combine the solid from the dichloromethane tritutation with the purified filtrate to give the desired compound (24.88 g, 90% total yield).

後処理

  1. washwash with water (3×500 mL) and saturated aqueous sodium chloride (200 mL)
  2. extractionExtract the aqueous washes with diethyl ether (3×)
  3. washwash with saturated aqueous sodium chloride
  4. dry with materialdry (magnesium sulfate)
  5. filtrationfilter through a pad of silica gel
  6. concentrationconcentrate
  7. temperaturecool
  8. filtrationfilter solid
  9. washeluting with 5:95 ethyl acetate

出典と根拠

ORDレコード
ord-970eee6e92f04994abac49288fa7b638
出典データセット
uspto-grants-2010_06
特許番号
US07745438B2

関連ノート

読み込み中…