1-Bromooctadecane → HCID 21185159, compound

HRID 363544Notes

Reaction equation

HRID 363544 reaction equation
[Na].[OH:2][C:3]1[CH:17]=[CH:16][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>C(O)C.[I-].[Na+]>[CH2:19]([O:2][C:3]1[CH:17]=[CH:16][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH3:19])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 3

HCID 82181-BromooctadecaneHCID 691504,4'-DihydroxybenzophenoneHCID 5360545Sodium

Product 1

HCID 21185159HCID 21185159, compoundYield 84.9%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 702EthanolSolvent

Procedure

Sodium metal (0.46 g, 20 mmol) was dissolved in ethanol (50 mL) and 4,4'-dihydroxybenzophenone (1.0 g, 4.67 mmol) was added followed by 1-bromooctadecane (7.8 g, 23.4 mmol) and a catalytic amount of sodium iodide (approximately 30 mg) and the reaction mixture was refluxed for 48 hours. The resulting suspension was cooled and filtered. The solid was washed with dichloromethane followed by hexane and the white solid was dried to afford compound 22 (2.85 g, 84.8% yield). 1H NMR (300 MHz, pyridine-d5) δ7.95 (d, J=8.7 Hz, 4H, aryl), 7.09 (d, J=8.7 Hz, 4H, aryl), 4.05 (t, J=6.6 Hz, 4H, 2×OCH2), 1.80 (tt, J=6.6 and 7.5 Hz, 4H), 1.48 (m, 4H), 1.33 (brS, 60H), 0.87 (t, J=6.6 Hz, 6H, 2×CH3).

Workup

  1. temperatureThe resulting suspension was cooled
  2. filtrationfiltered
  3. washThe solid was washed with dichloromethane
  4. customthe white solid was dried

Sources & evidence

ORD record
ord-b2334dea92dc432c8461799705819a55
Source dataset
uspto-grants-1999_02
Patent number
US05874532

Reaction notes

Loading…