1-Octanol, 8-bromo- → 8-(3-Nitro-4-phenylphenoxy)octan-1-ol

HRID 1518635Notes

Reaction equation

HRID 1518635 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:16])[CH:7]=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([O-:3])=[O:2].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26]>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[O:16][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 1626071-Octanol, 8-bromo-HCID 121698073-Nitro-4-phenylphenol

Product 1

HCID 665973428-(3-Nitro-4-phenylphenoxy)octan-1-olYield 89.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

3-Nitro-4-phenylphenol (860 mg, 4.0 mmol) was dissolved in N,N-dimethylformamide (40 mL), followed by addition of 8-bromo-1-octanol (1.86 g, 6.0 mmol). After stirring at 50° C. for 5 hours, the reaction solution was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography to obtain 8-(3-nitro-4-phenylphenoxy)octan-1-ol (1.23 g).

Workup

  1. extractionthe reaction solution was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-ec219bd6a3c94c4fbd8d69f9687515a2
Source dataset
uspto-grants-2015_07
Patent number
US09072734B2

Reaction notes

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