2-Methyl-2-butene → 2-methoxy-5-(trifluoromethoxy)benzoic Acid

HRID 582084

反応式

HRID 582084 の反応式
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:7][C:4]=1[CH:5]=[O:6].CC(=CC)C.O.P([O-])(O)(O)=[O:23].[Na+].Cl([O-])=O.[Na+].[OH-].[Na+]>C(O)(C)(C)C.O.C(OCC)(=O)C.CCCCCC>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:13])([F:14])[F:15])=[CH:7][C:4]=1[C:5]([OH:23])=[O:6]

参加物

9

反応物 5

HCID 105532-Methyl-2-buteneHCID 14798Sodium HydroxideHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 27833642-Methoxy-5-(trifluoromethoxy)benzaldehydeHCID 23668197Sodium Chlorite

生成物 1

HCID 27752862-methoxy-5-(trifluoromethoxy)benzoic Acid

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6386tert-Butanol溶媒HCID 21226206Ethyl acetate hexane溶媒

実験手順

According to the method of Heterocycles, 16, 2091 (1981), combine 2-methoxy-5-trifluoromethoxybenzaldehyde (0.58 g, 2.65 mmol) and 2-methylbut-2-ene (37 mL) in t-butanol (16 mL). Add dropwise a solution of sodium dihydrogen phosphate hydrate (0.92 g) and sodium chlorite (0.42 g, 4.7 mmol) in water (10 mL). After 4 hours, adjust the pH of the reaction mixture to about 8 to 9 using a 1M aqueous sodium hydroxide solution. Evaporate the reaction mixture in vacuo at about ambient temperature to remove most of the t-butanol. Add water (40 mL) and extract three times with hexane (10 mL). Adjust the pH of the aqueous layer to about 1 using a 1M aqueous hydrochloric acid solution and extract five times with diethyl ether. Combine the organic layers, dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 1/1 ethyl acetate/hexane containing 0.5% acetic acid to give 2-methoxy-5-trifluoromethoxybenzoic acid: Rf =0.34 (silica gel, 1/1 ethyl acetate/hexane containing 0.5% acetic acid).

後処理

  1. customEvaporate the reaction mixture in vacuo at about ambient temperature
  2. customto remove most of the t-butanol
  3. extractionAdd water (40 mL) and extract three times with hexane (10 mL)
  4. extractionextract five times with diethyl ether
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. customevaporate in vacuo
  8. customto give a residue

出典と根拠

ORDレコード
ord-885b6da9283e4854aeb5663ba405df4a
出典データセット
uspto-grants-1999_07
特許番号
US05922737

関連ノート

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