1,2-Dichloroethane → HCID 131727863, compound

HRID 251715Notes

Reaction equation

HRID 251715 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

Procedure

Next, 62.5 g of the 4,6-di(1-adamantyl)-1,3-bis(4-carboxy-phenoxy)benzene dipotassium salt obtained above (90 mmol), 200 mL of 1,2-dichloroethane and a stirrer were charged in a 2 L recovery flask. Then, 178.5 g of thionyl chloride mol) was gradually added thereto with agitating at 5° C. or less. After the addition, 1.5 mL of N,N-dimethylformamide and 1.5 g of hydroquinone were added and agitated at 45 to 50° C. for three hours. After reaction solution was filtered, solvent was removed from the reaction solution under reduced pressure. Solid thus obtained was washed with hexane and then recrystallized with diethyl ether, thus obtaining 38.9 g of 4,6-di(1-adamantyl)-1,3-bis(4-carboxy-phenoxy)benzene-dichloride (59.4 mmol; yield: 66.0%).

Workup

  1. additionwere charged in a 2 L recovery flask
  2. additionwere added
  3. stirringagitated at 45 to 50° C. for three hours
  4. customAfter reaction solution
  5. filtrationwas filtered
  6. customsolvent was removed from the reaction solution under reduced pressure
  7. customSolid thus obtained
  8. washwas washed with hexane
  9. customrecrystallized with diethyl ether

Sources & evidence

ORD record
ord-c3eaca3d13a3456aa9a130c67cbd106b
Source dataset
uspto-grants-2011_01
Patent number
US07863347B2

Reaction notes

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