Hydrochloric Acid → HCID 70026978, compound

HRID 397587Notes

Reaction equation

HRID 397587 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([CH3:27])[CH:21]=2)[C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].Cl.[Cl:35][CH2:36][CH2:37][N:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1.Cl>C1C=CC=CC=1.CC(C)=O>[ClH:35].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:36][CH2:37][N:38]3[CH2:42][CH2:41][CH2:40][CH2:39]3)=[C:22]([CH3:27])[CH:21]=2)[C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 11256744Phenol, 4-[(4-methoxyphenyl)-1-naphthalenylmethyl]-2-methyl-

Product 1

HCID 70026978HCID 70026978, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 241BenzeneSolvent

Procedure

A mixture of (4-methoxyphenyl)-(3-methyl-4-hydroxyphenyl)-naphth-1-yl-methane (0.3 gm, 0.008 mol), anhydrous K2CO3 (2.0 gm), 1-(2-chloroethyl)pyrrolidine hydrochloride (0.3 gm, 0.0017 mol) and anhydrous acetone (25 ml) was refluxed for 10 hrs, K2CO3 was filtered off, acetone was distilled off, and the residue was diluted with water. The reaction mixture was extracted with ethyl acetate washed with water, dried over Na2SO4 and concentrated to give an oil. This oil was passed through basic alumina using benzene as eluent. Solvent was distilled off. The oil thus obtained was treated with ethanolic HCl. The solvent was evaporated and compound was crystallized with absolute alcohol and anhydrous ether to give the title compound as a salt of general formula I. Yield 170 mg(46%).

Workup

  1. temperaturewas refluxed for 10 hrs
  2. filtrationK2CO3 was filtered off
  3. distillationacetone was distilled off
  4. additionthe residue was diluted with water
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customto give an oil
  10. distillationSolvent was distilled off
  11. customThe oil thus obtained
  12. customThe solvent was evaporated
  13. customcompound was crystallized with absolute alcohol and anhydrous ether

Sources & evidence

ORD record
ord-a52ed35743234d359697162520137023
Source dataset
uspto-grants-2003_08
Patent number
US06610705B1

Reaction notes

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