Benzene → HCID 20257375, compound

HRID 1583946Notes

Reaction equation

HRID 1583946 reaction equation
C1C=CC=CC=1.[CH2:7]([N:14]1[C:23]2[C:18](=[CH:19][C:20]([CH:24]([CH3:28])[C:25]([OH:27])=[O:26])=[CH:21][CH:22]=2)[CH2:17][CH2:16][C:15]1([CH3:30])[CH3:29])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:42][C:43]1[CH:50]=[CH:49][C:46]([CH2:47]O)=[CH:45][CH:44]=1>O>[CH2:7]([N:14]1[C:23]2[C:18](=[CH:19][C:20]([CH:24]([CH3:28])[C:25]([O:27][CH2:47][C:46]3[CH:49]=[CH:50][C:43]([Cl:42])=[CH:44][CH:45]=3)=[O:26])=[CH:21][CH:22]=2)[CH2:17][CH2:16][C:15]1([CH3:29])[CH3:30])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 133974-Chlorobenzyl alcoholHCID 13206084HCID 13206084, compound2×

Product 1

HCID 20257375HCID 20257375, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 30 ml of benzene were added 3.2 g of 2-(1-benzyl-1,2,3,4-tetrahydro-2,2-dimethylquinolin-6-yl)propionic acid (Compound 54), 4,4 g of p-toluenesulfonic acid and 14.3 g of 4-chlorobenzyl alcohol. The solution was heated and refluxed with removing water. The reaction mixture was concentrated, followed by washed petroleum ether and addition of ethyl acetate. Then the mixture was washed with sodium hydrogencarbonate, water and saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by column chromatography on silica gel (Hexan acetate) to give 3.7 g of 4-chlorobenzyl 2-(1-benzyl-1,2,3,4-tetrahydro-2,2-dimethylquinolin-6-yl)propionate (Compound 59).

Workup

  1. temperatureThe solution was heated
  2. concentrationThe reaction mixture was concentrated
  3. washby washed
  4. additionpetroleum ether and addition of ethyl acetate
  5. washThen the mixture was washed with sodium hydrogencarbonate, water and saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off
  8. customthe residue was purified by column chromatography on silica gel (Hexan acetate)

Sources & evidence

ORD record
ord-93ec5daa38604a3e947c6fecdb1c6ad0
Source dataset
uspto-grants-1985_11
Patent number
US04555513

Reaction notes

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