Bromobenzene → HCID 17747909, compound

HRID 1593795

Reaction equation

HRID 1593795 reaction equation
[K].[CH2:2]([C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].Br[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CN(C)C(=O)C>O>[CH2:2]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:18]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 7961BromobenzeneHCID 31374DimethylacetamideHCID 68146Hydrogenated cardanolHCID 5462222Potassium

Product 1

HCID 17747909HCID 17747909, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

To a round bottom flask containing 111 g potassium salt of 3-pentadecylphenol (0.32 mol) was added 50.88 g (0.32 mol) of bromobenzene, followed by 2.22 g Cu powder (2 wt %) along with 150 ml N,N-dimethylacetamide. The reaction mixture was then heated at 150° C. for 8 hours. After completion of the reaction the obtained dark colored solution was poured into 500 ml water; the Cu salts were removed by filtration; The filtrate was extracted with ethyl acetate, thoroughly washed with water followed by saturated aqueous sodium chloride solution and dried over sodium sulfate. Solvent evaporation yielded crude 1-pentadecyl-3-phenoxy benzene. Pure 1-pentadecyl-3-phenoxy benzene was obtained after silica gel (60-120 mesh) column chromatography (pet ether) 70 g (57% of the theoretical).

Workup

  1. customAfter completion of the reaction the obtained dark colored solution
  2. customthe Cu salts were removed by filtration
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washthoroughly washed with water
  5. dry with materialdried over sodium sulfate
  6. customSolvent evaporation
  7. customyielded crude 1-pentadecyl-3-phenoxy benzene

Sources & evidence

ORD record
ord-871dc23d10af4275b51cbfd6aafdb0a9
Source dataset
uspto-grants-2007_11
Patent number
US07297822B2

Linked notes

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