1-Bromooctadecane → HCID 21185159, compound

HRID 611748Notes

Reaction equation

HRID 611748 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) δ 7.95 (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-9cf03ec012af434eb884580c96fc281f
Source dataset
uspto-grants-1999_12
Patent number
US06001966

Reaction notes

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