Diphenyl Ether → 2-allyl-4-nitrophenol

HRID 2294963Notes

Reaction equation

HRID 2294963 reaction equation
[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]

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 220100Allyl p-nitrophenyl ether

Product 1

HCID 2584392-allyl-4-nitrophenol

Conditions

Temperature
250 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-f24128342ad54936a7e7a6bec61319fd
Source dataset
uspto-grants-1997_11
Patent number
US05691349

Reaction notes

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