1-Bromododecane → HCID 23075052, compound

HRID 1766630Notes

Reaction equation

HRID 1766630 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 (8.09, 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 recrystalized 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 recrystalized from isopropanol

Sources & evidence

ORD record
ord-bf8f58f62c8e4386bde94e295e255612
Source dataset
uspto-grants-2007_06
Patent number
US07230122B2

Reaction notes

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