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

HRID 374960노트

반응식

HRID 374960 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-49103b2092984fb4bd2ab72070fd6d7b
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05482974

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