Nitric Acid → HCID 22922925, 화합물

HRID 1683133노트

반응식

HRID 1683133 반응식
[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:23]([O-])([OH:25])=[O:24].O>C(O)(=O)C>[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[CH:18][C:19]([OH:22])=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=2)=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 944Nitric AcidHCID 962WaterHCID 229229204-Benzoyloxy-4'-hydroxybiphenyl

생성물 1

HCID 22922925HCID 22922925, 화합물수율 96%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

To an argon-flushed flask containing a suspension 0.486 g (1.68 mmol) of 4'hydroxy-4-biphenylyl benzoate in 10 ml of acetic acid at 10°-15° C., 0.345 ml of HNO3 (d: 1.41) was added dropwise (about a drop per min). Then the reaction mixture was vigorously stirred at the same temperature for 30 min. Water (40 ml) was added and the mixture was again stirred for 30 min. The yellow precipitate was filtered, washed several times with water, dried and purified by flash chromatograPhY on silica gel using dichloromethane/hexanes [65/35] as eluent to give 4'-hydroxy-3'-nitro-4-biphenylyl benzoate (compound 15, Scheme II) as a yellow solid (0.539 g, 96%). This material was recrystallized from ethanol to give product of mp. 163° C.;. Rf [hexanes/dichloromethane 40/60]: 0.42; 1H NMR (300 MHz, CDCl3): δ 7.25(d, 1 H, J=8.7 Hz), 7.33(d, 2 H, J=8.7 Hz), 7.50-7.70(m, 5 H), 7.84(dd, 1 H, J=2.7 Hz, J=8.7 Hz), 8.23(d, 2 H, J=7.2 Hz), 8.32(d, 1 H, J=2.7 Hz), 10.60(s, 1 H); 13C NMR (300 MHz, CDCL3): δ 120.54, 122.45, 122.81, 127.85, 128.65, 129.33, 130.23, 133.04, 133.78, 136.04, 136.22, 150.91, 154.44, 165.15; IR (CHCL3): 3250(broad), 3020, 1740, 1620, 1540, 1510, 1490, 1325, 1270, 1225, 1220, 1170, 1080, 1065, 1025, 1000, 850 cm-1 ; Mass spectrum, m/z(rel.intensity): 335(M+ 7) , 105(100) , 77(16).

후처리

  1. customTo an argon-flushed flask
  2. stirringthe mixture was again stirred for 30 min
  3. filtrationThe yellow precipitate was filtered
  4. washwashed several times with water
  5. customdried
  6. custompurified by flash chromatograPhY on silica gel

출처 및 근거

ORD 기록
ord-377cbec9232d48fdadb7e308aed5ab68
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05637256

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