Sodium Chlorite → 2-Cyclopropyl-6-ethyl-benzoic acid

HRID 1950909노트

반응식

HRID 1950909 반응식
[CH:1]1([C:4]2[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][CH3:13])[C:5]=2[CH:6]=[O:7])[CH2:3][CH2:2]1.Cl([O-])=[O:15].[Na+].P([O-])(O)(O)=O.[Na+]>C(O)(C)(C)C.CC(=CC)C.O>[CH:1]1([C:4]2[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][CH3:13])[C:5]=2[C:6]([OH:15])=[O:7])[CH2:2][CH2:3]1

참가 물질

7

반응물 3

HCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 589519652-Cyclopropyl-6-ethyl-benzaldehyde

생성물 1

HCID 580628792-Cyclopropyl-6-ethyl-benzoic acid

시약·촉매·용매 3

HCID 962Water용매HCID 6386tert-Butanol용매HCID 105532-Methyl-2-butene용매

실험 절차

2-Cyclopropyl-6-ethyl-benzaldehyde (CAS 945408-11-7) (500 mg, 2.9 mmol) was dissolved in 3.5 mL tert butanol and 1.7 mL 2-methyl-2-butene. At 0° C. a solution of sodium chlorite (80% purity, 422 mg, 3.8 mmol) and sodium dihydrogenphosphate (452 mg, 3.8 mmol) in 3 mL water was added slowly. The reaction mixture was stirred at room temperature over night. The solvents were evaporated off. The residue was taken up in 1N sodium hydroxide solution and was extracted with tert butyl methylether. The aqueous phase was adjusted at pH 1 with 25% HCl and extracted twice with tert butyl methylether. The combined organic phases were dried on sodium sulfate, filtered and evaporated. The crude product was used without any further purification, white solid (412 mg, 75%), MS: m/e=189.3 [(M−H)−].

후처리

  1. customThe solvents were evaporated off
  2. extractionwas extracted with tert butyl methylether
  3. extractionextracted twice with tert butyl methylether
  4. customThe combined organic phases were dried on sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was used without any further purification, white solid (412 mg, 75%), MS

출처 및 근거

ORD 기록
ord-fd3978e2430d4230acee5963576eccba
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404673B2

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