Citric Acid → HCID 86751488, compound

HRID 1938639Notes

Reaction equation

HRID 1938639 reaction equation
Cl.[CH2:2]([N:4]([CH2:31][CH3:32])[CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13](/[C:16](/[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:17](\[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)/[Cl:18])=[CH:12][CH:11]=1)[CH3:3].ClCCl.[OH-].[Na+].[C:38]([OH:50])(=[O:49])[CH2:39][C:40]([CH2:45][C:46]([OH:48])=[O:47])([C:42]([OH:44])=[O:43])[OH:41]>O.CC(C)=O>[C:38]([OH:50])(=[O:49])[CH2:39][C:40]([CH2:45][C:46]([OH:48])=[O:47])([C:42]([OH:44])=[O:43])[OH:41].[CH2:31]([N:4]([CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13](/[C:16](/[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:17](\[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)/[Cl:18])=[CH:12][CH:11]=1)[CH3:32]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 21469779HCID 21469779, compound

Product 1

HCID 86751488HCID 86751488, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

Combine (E)-1-[4-(4-diethylaminobutoxy)phenyl]-1,2-diphenyl-2-chloro-ethylene hydrochloride salt (138.4 g, 0.294 mol) and dichloromethane. Add with stirring a solution of sodium hydroxide (12.8 g) in water (100 mL). After 30 minutes, separate the layers and extract the aqueous layer with dichloromethane. Dry the combined organic layers over MgSO4, filter, and evaporate in vacuo to give a residue. Combine the residue and acetone (1 L). Filter and combine the filtrate with a solution of citric acid (56.5 g, 0.294 mol) in acetone (2 L). Allow to stand at ambient temperature to give a solid. Collect the solid by filtration, rinse with acetone, and dry to give the title compound as a solid: mp; 133°-135° C.

Workup

  1. additionAdd
  2. customseparate the layers
  3. extractionextract the aqueous layer with dichloromethane
  4. dry with materialDry the combined organic layers over MgSO4
  5. filtrationfilter
  6. customevaporate in vacuo
  7. customto give a residue
  8. filtrationFilter
  9. customto stand at ambient temperature
  10. customto give a solid
  11. customCollect the solid
  12. filtrationby filtration
  13. washrinse with acetone
  14. customdry

Sources & evidence

ORD record
ord-eb63ea641ff04a168f0202851448b1b7
Source dataset
uspto-grants-1997_12
Patent number
US05693674

Reaction notes

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