Sodium Hydroxide → 3-(4,5-Dihydro-1H-imidazol-2-yl)phenol

HRID 1581782Notes

Reaction equation

HRID 1581782 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](OC)=O.S(C1C=CC(C)=CC=1)(O)(=O)=O.[NH2:23][CH2:24][CH2:25][NH2:26].[OH-].[Na+]>>[OH:1][C:2]1[CH:3]=[C:4]([C:5]2[NH:23][CH2:24][CH2:25][N:26]=2)[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 88068Methyl 3-HydroxybenzoateHCID 2250301,2-Ethanediamine, 4-methylbenzenesulfonate (1:?)

Product 1

HCID 162181653-(4,5-Dihydro-1H-imidazol-2-yl)phenolYield 22.3%

Conditions

Temperature
210 °C

Procedure

A mixture of methyl 3-hydroxybenzoate (5.48 g, 36.0 mmol) and 1,2-diaminoethane monotosylate (9.85 g, 42.4 mmol) is heated at 210° C. for 7 hours. After cooling, the mixture is stirred with aqueous 2N sodium hydroxide and extracted with ethyl acetate. The precipitate which formed and is present in the aqueous layer is collected by filtration and dried in vacuo to give 1.3 g (22%) of 2-(3-hydroxyphenyl)imidazoline.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. customThe precipitate which formed
  4. filtrationis collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-7785899d448841c499729958b4af60f4
Source dataset
uspto-grants-2004_05
Patent number
US06730792B2

Reaction notes

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