Diphenyl Ether → 2-allyl-4-nitrophenol

HRID 2294963노트

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HRID 2294963 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10]CC=C)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:14]1(OC2C=CC=CC=2)[CH:19]=CC=C[CH:15]=1>>[CH2:19]([C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=[CH:8][C:7]=1[OH:10])[CH:14]=[CH2:15]

참가 물질

3

반응물 2

HCID 7583Diphenyl EtherHCID 220100Allyl p-nitrophenyl ether

생성물 1

HCID 2584392-allyl-4-nitrophenol

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온도
250 °C

실험 절차

A mixture of allyl 4-nitrophenyl ether (78 g) and diphenyl ether (150 ml) was heated at 250° C. for 30 minutes. The reaction mixture was cooled to ambient temperature, and partitioned between diethyl ether and 2M aqueous sodium hydroxide solution. The aqueous layer was separated and acidified to pH3 with concentrated hydrochloric acid. The aqueous mixture was extracted with ethyl acetate the ethyl acetate extract dried (MgSO4) and evaporated. The residue was purified by column chromatography on silica gel (Merck 7736) using a gradient of 0% to 20% methanol in dichloromethane as eluent to give 2-allyl-4-nitrophenol (21.4 g); microanalysis, found: C, 60.6; H, 5.1; N, 7.9%; C9H9 NO3 requires: C, 60.3; H, 5.06; N, NMR): 3.36(2H,d), 5.1(2H,m), 5.98(1H,m), 6.97(1H,d), 8.0(2H,m); m/z 197 (M+NH4).

후처리

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. custompartitioned between diethyl ether and 2M aqueous sodium hydroxide solution
  3. customThe aqueous layer was separated
  4. extractionThe aqueous mixture was extracted with ethyl acetate the ethyl acetate
  5. extractionextract
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel (Merck 7736)

출처 및 근거

ORD 기록
ord-f24128342ad54936a7e7a6bec61319fd
출처 데이터셋
uspto-grants-1997_11
특허 번호
US05691349

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