Citric Acid → HCID 86751488, compound

HRID 1938641Notes

Reaction equation

HRID 1938641 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].C(OCC)(=O)C.[OH-].[Na+].[C:41]([OH:53])(=[O:52])[CH2:42][C:43]([CH2:48][C:49]([OH:51])=[O:50])([C:45]([OH:47])=[O:46])[OH:44]>O.CC(C)=O>[C:41]([OH:53])(=[O:52])[CH2:42][C:43]([CH2:48][C:49]([OH:51])=[O:50])([C:45]([OH:47])=[O:46])[OH:44].[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 8857Ethyl AcetateHCID 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 ethyl acetate (75 L). Add with stirring a solution of sodium hydroxide (3.0 kg, 75 mol) in water (20 L). After dissolution, separate the layers, dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Combine the residue and acetone (80 L). Filter and combine the filtrate with a solution of citric acid (3.6 kg, 18.8 mol) in acetone (20 L) and stir to give a solid. After 18 hours, collect the solid by filtration, rinse with acetone, and dry to give the title compound as a solid. Elemental Analysis calculated for C28H32ClNO.C6H8O7 : C, 65.22; H, 6.44; N, 2.24. Found: C, 65.19; H, 6.29; N, 2.14.

Workup

  1. additionAdd
  2. dissolutionAfter dissolution
  3. customseparate the layers
  4. dry with materialdry the organic layer over MgSO4
  5. filtrationfilter
  6. customevaporate in vacuo
  7. customto give a residue
  8. filtrationFilter
  9. customto give a solid
  10. customcollect the solid
  11. filtrationby filtration
  12. washrinse with acetone
  13. customdry

Sources & evidence

ORD record
ord-5d68fe3114a64f329d49a0044220683a
Source dataset
uspto-grants-1997_12
Patent number
US05693674

Reaction notes

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