Urea → 1,3-Dihydro-5-isobenzofuranol

HRID 398088노트

반응식

HRID 398088 반응식
[CH2:1]1[C:5]2[CH:6]=[CH:7][C:8](N)=[CH:9][C:4]=2[CH2:3][O:2]1.N([O-])=[O:12].[Na+].NC(N)=O>O.OS(O)(=O)=O>[CH2:1]1[C:5]2[CH:6]=[CH:7][C:8]([OH:12])=[CH:9][C:4]=2[CH2:3][O:2]1

참가 물질

6

반응물 3

HCID 1176UreaHCID 124453391,3-Dihydro-2-benzofuran-5-amineHCID 23668193Sodium Nitrite

생성물 1

HCID 111477471,3-Dihydro-5-isobenzofuranol수율 36%

시약·촉매·용매 2

HCID 962Water용매3회HCID 1118Sulfuric Acid용매2회

반응 조건

온도
0 °C

실험 절차

1,3-Dihydro-2-benzofuran-5-amine (prepared according to U.S. Pat. No. 4,000,286) (2.7 g, 20 mmol) was dissolved in a mixture of water (300 mL) and conc. H2SO4 (21 mL), cooled to 0° C. and NaNO2 (1.43 g, 20.7 mmol) in water (10 mL) was added over 15 min. After stirring at 0° C. for 1 h the mixture was allowed to stir at 10° C. for 30 min and urea was added until a negative test with starch/KI paper was observed. The solution was then poured over 2 min into a mixture of water (180 mL) and conc. H2SO4 (12.6 mL) at 90° C. and stirred at this temperature for 1.5 h. The hot mixture was filtered then allowed to cool to room temperature. The aqueous mixture was extracted with EtOAc (2×100 mL) and the combined organic layers were dried (MgSO4) and evaporated to give the title phenol (974 mg, 36%) as a cream solid; δH (CDCl3, 400 MHz) 5.03 (4H, s), 6.71 (2H, m), 7.08 (1H, d).

후처리

  1. stirringto stir at 10° C. for 30 min
  2. stirringstirred at this temperature for 1.5 h
  3. filtrationThe hot mixture was filtered
  4. temperatureto cool to room temperature
  5. extractionThe aqueous mixture was extracted with EtOAc (2×100 mL)
  6. dry with materialthe combined organic layers were dried (MgSO4)
  7. customevaporated

출처 및 근거

ORD 기록
ord-a10c38494daa46979da452bf1e03cf81
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610747B2

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