Water → HCID 70454169, compound

HRID 1381234Notes

Reaction equation

HRID 1381234 reaction equation
[CH2:1]([N:3]1[CH2:7][CH:6]2[O:8][CH:5]2[CH2:4]1)[CH3:2].[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:11]=1[OH:17].[OH-].[Na+].O>Cl.C(Cl)Cl>[ClH:9].[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:11]=1[O:17][C@@H:6]1[CH2:7][N:3]([CH2:1][CH3:2])[CH2:4][C@H:5]1[OH:8]

Participants

7

Reactant 4

HCID 962WaterHCID 68992,6-DichlorophenolHCID 14798Sodium HydroxideHCID 13320194N-ethyl-3,4-epoxypyrrolidine

Product 1

HCID 70454169HCID 70454169, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 11.3 g. (0.10 mole) of 1-ethyl-3,4-epoxypyrrolidine, 18.0 g. (0.11 mole) of 2,6-dichlorophenol and 2 drops concentrated hydrochloric acid was heated on a steam bath overnight. The oil was dissolved in methylene chloride and wahed with three 50-ml. portions of 5% sodium hydroxide an one 50-ml. portion of water. The methylene chloride solution was dried over anhydrous sodium sulfate, concentrated and chromatogrpahed on silica gel to give 12.9 g. (47%) of and oil residue. The oil was converted to the hydrchloride and recrystallized from isopropyl alcohol-diethyl ether to yield 12.3 g. (39%), m.p. 160°-162° C.

Workup

  1. additionA mixture of 11.3 g
  2. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customto give 12.9 g
  5. customrecrystallized from isopropyl alcohol-diethyl ether
  6. customto yield 12.3 g

Sources & evidence

ORD record
ord-585494d46a93476a8b53bd5ed86d0bcd
Source dataset
uspto-grants-1986_04
Patent number
US04585785

Reaction notes

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