Ammonium Chloride → Tris(2,4-dimethoxyphenyl)methanol

HRID 516797

反応式

HRID 516797 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][CH3:11].[CH3:12][O:13][C:14]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:15]=1[C:16](OC)=[O:17].[NH4+].[Cl-]>CCOCC>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:16]([OH:17])([C:15]2[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:14]=2[O:13][CH3:12])[C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=2[O:10][CH3:11])=[C:3]([O:10][CH3:11])[CH:4]=1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 872661-Bromo-2,4-dimethoxybenzeneHCID 137451Benzoic acid, 2,4-dimethoxy-, methyl ester

生成物 1

HCID 44630337Tris(2,4-dimethoxyphenyl)methanol

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

Add (4.23 g, 19.47 mmol) 1-bromo-2,4-dimethoxybenzene to an appropriately sized round bottom flask. Attach a rubber septum to seal the flask. Insert a needle into the septum as a vent and flush the round bottom flask with nitrogen for about 10 minutes. Add anhydrous ether (80 mL), followed by the drop wise addition of n-butyllithium in hexane (1.6M, 12.2 mL). Stir the cloudy mixture for 10 minutes and keep the round bottom flask on ice. Dissolve (2.20 g, 9.74 mmol) of methyl 2,4-dimethoxybenzoate in about 20 ml of anhydrous ether (if needed, more than about 20 ml can be used), and then add this drop wise to the reaction mixture. After the addition is complete, stir the reaction mixture for about 3 minutes longer. Pour the reaction mixture into a separatory funnel containing 5% NH4Cl (aq) (50 mL) and shake until a color change is observed (pale orange). The layers are allowed to separated, and dry the top ether layer with about 5 g anhydrous Na2SO4, filter, and the volatiles were removed in a rotary evaporator to dryness at 35-40° C. under 400 mbar. Place the crude oil of hexamethoxy red (yellow-orange in color) into the freezer. Yield is about 3.1 g.

後処理

  1. customto seal the flask
  2. customInsert a needle into the septum as a vent and flush the round bottom flask with nitrogen for about 10 minutes
  3. additionAdd anhydrous ether (80 mL), followed by the drop wise addition of n-butyllithium in hexane (1.6M, 12.2 mL)
  4. additionadd this drop wise to the reaction mixture
  5. additionAfter the addition
  6. stirringstir the reaction mixture for about 3 minutes longer
  7. additionPour the reaction mixture into a separatory funnel
  8. customto separated
  9. dry with materialdry the top ether layer with about 5 g anhydrous Na2SO4
  10. filtrationfilter
  11. customthe volatiles were removed in a rotary evaporator to dryness at 35-40° C. under 400 mbar

出典と根拠

ORDレコード
ord-46f242c095aa45f9b22bb4b4a66bf3c2
出典データセット
uspto-grants-2015_08
特許番号
US09115066B2

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