1,2-Dichloroethane → HCID 131727863, compound

HRID 1994657Notes

Reaction equation

HRID 1994657 reaction equation
[K].[K].[C:3]12([C:13]3[CH:18]=[C:17]([C:19]45[CH2:28][CH:23]6[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]6)[CH2:20]4)[CH2:26]5)[C:16]([O:29][C:30]4[CH:35]=[CH:34][C:33]([C:36]([OH:38])=[O:37])=[CH:32][CH:31]=4)=[CH:15][C:14]=3[O:39][C:40]3[CH:45]=[CH:44][C:43]([C:46]([OH:48])=[O:47])=[CH:42][CH:41]=3)[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.[Cl:49]CCCl.S(Cl)([Cl:55])=O.C1(C=CC(O)=CC=1)O>CN(C)C=O>[Cl-:49].[Cl-:55].[C:3]12([C:13]3[CH:18]=[C:17]([C:19]45[CH2:20][CH:21]6[CH2:27][CH:25]([CH2:24][CH:23]([CH2:22]6)[CH2:28]4)[CH2:26]5)[C:16]([O:29][C:30]4[CH:31]=[CH:32][C:33]([C:36]([OH:38])=[O:37])=[CH:34][CH:35]=4)=[CH:15][C:14]=3[O:39][C:40]3[CH:45]=[CH:44][C:43]([C:46]([OH:48])=[O:47])=[CH:42][CH:41]=3)[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 785HydroquinoneHCID 24386Thionyl ChlorideHCID 67506602HCID 67506602, compound

Product 1

HCID 131727863HCID 131727863, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

In a 2 L four-neck flask provided with a thermometer, a Dimroth condenser and an agitator, the obtained 62.5 g of 4,6-di(1-adamantyl)-1,3-bis(4-carboxy-phenoxy)benzene dipotassium salt (0.09 mol) and 200 mL of 1,2-dichloroethane were charged and cooled to 0° C. 178.5 g of thionyl chloride (1.5 mol) was added dropwise at 5° C. or below for one hour. Then, 1.5 mL of dimethylformamide and 1.5 g of hydroquinone were added therein and the mixture was agitated at 45 to 50° C. for three hours. After cooling, crystal was removed therefrom by filtration and washed with 50 mL of chloroform. Filtrate and washing solution was condensed together under reduced pressure at 40° C. or less, and a residue obtained was subject to two times of extraction and filtration with 200 mL of diethyl ether. Diethyl ether was removed from an extract under reduced pressure to obtain a semisolid crude product. The semisolid crude product was washed with dried n-hexane and recrystallized with diethyl ether, thus obtaining 38.9 g of 4,6-di(1-adamantyl)-1,3-bis(4-carboxy-phenoxy)benzene dichloride (0.0594 mol; the yield was 66.0%).

Workup

  1. customIn a 2 L four-neck flask provided with a thermometer
  2. temperatureAfter cooling
  3. customcrystal was removed
  4. filtrationby filtration
  5. washwashed with 50 mL of chloroform
  6. washFiltrate and washing solution
  7. customcondensed together under reduced pressure at 40° C. or less
  8. customa residue obtained
  9. extractionwas subject to two times of extraction and filtration with 200 mL of diethyl ether
  10. customDiethyl ether was removed from
  11. extractionan extract under reduced pressure
  12. customto obtain a semisolid crude product
  13. washThe semisolid crude product was washed with dried n-hexane
  14. customrecrystallized with diethyl ether

Sources & evidence

ORD record
ord-a591621e05f84f80a307d7c1de5b4779
Source dataset
uspto-grants-2010_01
Patent number
US07652125B2

Reaction notes

Loading…