Potassium Permanganate → 2-[(1,1-Dimethylethyl)oxy]-6-chlorobenzoic acid

HRID 374960ノート

反応式

HRID 374960 の反応式
[CH3:1][C:2]([O:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:7]=1[CH:8]=[O:9])([CH3:4])[CH3:3].[OH:15]P([O-])(O)=O.[K+].[Mn]([O-])(=O)(=O)=O.[K+]>C(O)(C)(C)C>[CH3:4][C:2]([O:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:7]=1[C:8]([OH:15])=[O:9])([CH3:1])[CH3:3]

参加物

5

反応物 3

HCID 516875Potassium PermanganateHCID 516951Monobasic potassium phosphateHCID 189963802-[(1,1-Dimethylethyl)oxy]-6-chlorobenzaldehyde

生成物 1

HCID 189963762-[(1,1-Dimethylethyl)oxy]-6-chlorobenzoic acid収率 78%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

To a solution of 2-[(1,1-dimethylethyl)oxy]-6-chlorobenzaldehyde (8.40 g, 40.0 mmol) in t-butanol (200 mL) was added 1.25M KH2PO4 (pH 7, 200 mL) and 0.4M aqueous potassium permanganate (200 mL, 80 mmol). The reaction was stirred at room temperature for 3 h and was quenched by the addition of saturated aqueous sodium sulfite (200 mL). The brown suspension was acidified with 2N HCl with ice-cooling until the MnO2 dissolved (pH 4). The reaction was extracted with ethyl acetate (3 times) and the organic layers were washed with brine, dried (MgSO4) and concentrated to a white solid. The crude product was recrystallized from hexanes at 0° C. to afford 7.14 g (78%) of 2-[(1,1-dimethylethyl)oxy]-6-chlorobenzoic acid as white crystals: mp 117°-119° C.

後処理

  1. customwas quenched by the addition of saturated aqueous sodium sulfite (200 mL)
  2. temperaturecooling until the MnO2
  3. dissolutiondissolved (pH 4)
  4. extractionThe reaction was extracted with ethyl acetate (3 times)
  5. washthe organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated to a white solid
  8. customThe crude product was recrystallized from hexanes at 0° C.

出典と根拠

ORDレコード
ord-49103b2092984fb4bd2ab72070fd6d7b
出典データセット
uspto-grants-1996_01
特許番号
US05482974

反応ノート

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