1-Bromododecane → HCID 23075052, compound

HRID 227211Notes

Reaction equation

HRID 227211 reaction equation
[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[C:5]([OH:17])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>CC(C)=O>[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[C:5]([O:17][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH3:25])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 89191-BromododecaneHCID 11430Potassium CarbonateHCID 28259241-Chloro-4-hydroxythioxanthone

Product 1

HCID 23075052HCID 23075052, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Chloro-4-dodecyloxythioxanthone was prepared as follows. A solution of 1-chloro-4-hydroxythioxanthone (14.0 g, 0.05 mol), K2CO3 (8.0 g, 0.06 mol) in acetone (250 mL) was stirred and refluxed for 10 min. Bromododecane (20.0 g, 0.08 mol) was added and the resulting mixture was stirred for 24 h under reflux. The reaction was then cooled to room temperature and quenched with water (500 mL). The obtained solid was filtered, washed with water, purified by recrystallized from isopropanol to give the 1-chloro-4-dodecyloxythioxanthone (14.3 g, 62%) with mp 79-80° C. The identity of this compound was shown by 1H NMR to have the following structure:

Workup

  1. custom1-Chloro-4-dodecyloxythioxanthone was prepared
  2. temperaturerefluxed for 10 min
  3. temperatureunder reflux
  4. customquenched with water (500 mL)
  5. filtrationThe obtained solid was filtered
  6. washwashed with water
  7. custompurified
  8. customby recrystallized from isopropanol

Sources & evidence

ORD record
ord-80a9f63cf4254dba87ce869e167cfda3
Source dataset
uspto-grants-2009_07
Patent number
US07560219B2

Reaction notes

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