4-Nitrophenol → 1-(4-Nitrophenoxy)-3-iodopropane

HRID 1091084Notes

Reaction equation

HRID 1091084 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:30][CH2:31][CH2:32][CH2:33]O.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:33][CH2:32][CH2:31][I:30])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 11776TriphenylphosphineHCID 693903-Iodo-1-propanolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 156758901-(4-Nitrophenoxy)-3-iodopropaneYield 79.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a stirring solution of 4-nitrophenol (10.0 g, 71.94 mmol) in tetrahydrofuran (100 mL) at 0° C. was added triphenylphosphine (22.6 g, 86.33 mmol), 3-iodopropanol (16.73 g, 89.93 mmol), and diethylazodicarboxylate (14.3 mL, 86.33 mmol). The resulting mixture was stirred at 25° C. overnight. The mixture was partitioned between brine and ethyl acetate. The organic phase was dried and concentrated. The residue was triturated with 8:1 ether/ethyl acetate to induce the precipitation of 22 g of triphenylphosphine oxide which was separated by filtration. The filtrate was preabsorbed onto silica gel and flash-chromatographed (5:1 hexane/ethyl acetate) to afford 17.5 g (79%) of white solid product.

Workup

  1. customThe mixture was partitioned between brine and ethyl acetate
  2. customThe organic phase was dried
  3. concentrationconcentrated
  4. customThe residue was triturated with 8:1 ether/ethyl acetate
  5. customthe precipitation of 22 g of triphenylphosphine oxide which
  6. customwas separated by filtration
  7. customThe filtrate was preabsorbed onto silica gel
  8. customflash-chromatographed (5:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8af22632541945ffaa270021dc68b9b7
Source dataset
uspto-grants-1992_01
Patent number
US05084463

Reaction notes

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