4-Nitrophenol → 1-Nitro-4-(1,8-nonadiene-5-yloxy)benzene

HRID 876196Notes

Reaction equation

HRID 876196 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH:5]([OH:10])[CH2:6][CH2:7][CH:8]=[CH2:9].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[N+:30]([C:33]1[CH:38]=[CH:37][C:36](O)=[CH:35][CH:34]=1)([O-:32])=[O:31].CCOC(/N=N/C(OCC)=O)=O>C(OCC)(=O)C.CCCCCC.CCOCC.C1COCC1>[N+:30]([C:33]1[CH:38]=[CH:37][C:36]([O:10][CH:5]([CH2:6][CH2:7][CH:8]=[CH2:9])[CH2:4][CH2:3][CH:2]=[CH2:1])=[CH:35][CH:34]=1)([O-:32])=[O:31]

Participants

9

Reactant 4

HCID 9804-NitrophenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 118295421,8-Nonadien-5-ol

Product 1

HCID 867088781-Nitro-4-(1,8-nonadiene-5-yloxy)benzeneYield 65%

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 300 ml-capacity three neck flask containing a stirring bar and connected to a condenser was sufficiently dried. Then, a nitrogen atmosphere was established in the flask, and 1,8-nonadiene-5-ol (8) (3.72 g, 2.66 mmol), PPh3 (6.98 g, 2.66 mmol), and 4-nitrophenol (4.43 g, 3.19 mmol) were introduced into the flask. Dried THF (50 ml) was further added to the mixture, the mixture thus obtained was stirred at room temperature, DEAD (12.2 ml, 3.19 mmol) was then dropped into the flask, and the mixture thus obtained was stirred for 5 hours. When generation of ether was recognized by thin-layer chromatography (hexane:ethyl acetate=10:1), the solvent was distilled off under reduced pressure, the mixture was purified by flash chromatography on silica gel (hexane:ethyl acetate=10:1). Thus, 1-nitro-4-(1,8-nonadiene-5-yloxy)benzene (11) (4.731 g, 1.7 mmol, yield: 65%) was obtained as an intended compound. 1HNMR values of 1-nitro-4-(1,8-nonadiene-5-yloxy)benzene (11) are shown below.

Workup

  1. additionA 300 ml-capacity three neck flask containing a stirring bar
  2. customconnected to a condenser
  3. customwas sufficiently dried
  4. additionwere introduced into the flask
  5. customthe mixture thus obtained
  6. customthe mixture thus obtained
  7. stirringwas stirred for 5 hours
  8. distillationthe solvent was distilled off under reduced pressure
  9. customthe mixture was purified by flash chromatography on silica gel (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-ff6c5439f3a940789af650a2ac57a4dd
Source dataset
uspto-grants-2015_03
Patent number
US08987044B2

Reaction notes

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