2,6-Dimethylphenol → HCID 14623328, compound

HRID 1111356Notes

Reaction equation

HRID 1111356 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].Cl.[Cl:11][CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CC(CC)=O.[Na+].[I-]>[ClH:11].[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 113352,6-DimethylphenolHCID 11430Potassium CarbonateHCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride

Product 1

HCID 14623328HCID 14623328, compoundYield 64.8%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

46.7 g (0.38 mole) of 2,6-dimethylphenol, 65.0 g (0.38 mole) of N-(2-chloroethyl)pyrrolidine hydrochloride, 210.1 g (1.52 mole) of potassium carbonate and 2 g of NaI in 300 ml of ethyl methyl ketone were refluxed for 48 h. The reaction mixture was concentrated under reduced pressure, the residue was partitioned between water and ether, the organic phase was separated off, washed with water and dried, and excess ethereal hydrogen chloride solution was added. The precipitated product was recrystallized from 10/1 ethyl acetate/isopropanol. 63 g of N-[2-(2,6-dimethylphenoxy)ethyl]pyrrolidine hydrochloride were obtained.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between water and ether
  3. customthe organic phase was separated off
  4. washwashed with water
  5. customdried
  6. additionexcess ethereal hydrogen chloride solution was added
  7. customThe precipitated product was recrystallized from 10/1 ethyl acetate/isopropanol

Sources & evidence

ORD record
ord-8a90756ccf864e6bbefa0c5cd30d0a07
Source dataset
uspto-grants-1990_12
Patent number
US04980361

Reaction notes

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