1-Bromooctadecane → HCID 4442740, compound

HRID 1757796Notes

Reaction equation

HRID 1757796 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:29]([O:10][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=[CH:8][CH:7]=1)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]

Participants

5

Reactant 3

HCID 82181-BromooctadecaneHCID 111373-NitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 4442740HCID 4442740, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4.0 g (0.029 mol) of 3-nitrophenol, 10.5 g (0.032 mol) of 1-bromooctadecane and 6.0 g (0.043 mol) of anhydrous potassium carbonate in 75 ml of anhydrous DMF was stirred and heated at 75° for 23 hours. The solvent was removed at reduced pressure and water was added to the residue. The product was extracted with ether and the dried extract was concentrated at reduced pressure to a solid which was purified by HPLCusing 15% methylene chloride-hexane to give 9.0 g (80% yield) of 3-(octadecyloxy)nitrobenzene.

Workup

  1. temperatureheated at 75° for 23 hours
  2. customThe solvent was removed at reduced pressure and water
  3. additionwas added to the residue
  4. extractionThe product was extracted with ether
  5. extractionthe dried extract
  6. concentrationwas concentrated at reduced pressure to a solid which
  7. customwas purified

Sources & evidence

ORD record
ord-5ff683b079c048be836a0278f83a175c
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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