Diphenyl Ether → 2-allyl-4-nitrophenol

HRID 2294963ノート

反応式

HRID 2294963 の反応式
[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]

参加物

3

反応物 2

HCID 7583Diphenyl EtherHCID 220100Allyl p-nitrophenyl ether

生成物 1

HCID 2584392-allyl-4-nitrophenol

反応条件

温度
250 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f24128342ad54936a7e7a6bec61319fd
出典データセット
uspto-grants-1997_11
特許番号
US05691349

反応ノート

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