2,3-Dimethylphenol → Xibenolol

HRID 328880Notes

Reaction equation

HRID 328880 reaction equation
[C:1]([N:5]1[CH2:8][CH:7]([OH:9])[CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[C:10]1([OH:18])[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:11]=1[CH3:17].[OH-].[K+]>CCOCC>[CH3:17][C:11]1[C:12]([CH3:16])=[CH:13][CH:14]=[CH:15][C:10]=1[O:18][CH2:6][CH:7]([OH:9])[CH2:8][NH:5][C:1]([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 106872,3-DimethylphenolHCID 14797Potassium HydroxideHCID 2879861-tert-Butyl-3-hydroxyazetidine

Product 1

HCID 146256Xibenolol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
155 °C

Procedure

To a mixture of 6.5 parts of 1-(tert.-butyl)-3-azetidinol and 6.7 parts of 2,3-xylenol 0.2 part of potassium hydroxide was added, and the mixture was heated at 155° C. for 20 hours. The reaction mixture was cooled and then dissolved in 100 parts of ether. The solution was washed three times with 50 parts of 2N-sodium hydroxide aqueous solution and extracted three times with 2N-hydrochloric acid aqueous solution. The extract was washed with 50 parts of ether and was made alkaline by adding 2N-sodium hydroxide solution gradually thereto. Then, the ether extraction was conducted three times and the extract was condensed and allowed to stand in a cool place. As a result crystals were formed, which were recrystallized twice from ether to yield 8.3 parts of 1-(2',3'-dimethylphenyloxy)-3-(tert.-butylamino)-2-propanol having a melting point of 57° C. Results of infra-red spectrum analysis and ultraviolet ray absorption analysis of the product are as follows:

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled
  3. washThe solution was washed three times with 50 parts of 2N-sodium hydroxide aqueous solution
  4. extractionextracted three times with 2N-hydrochloric acid aqueous solution
  5. washThe extract was washed with 50 parts of ether
  6. additionby adding 2N-sodium hydroxide solution gradually
  7. extractionThen, the ether extraction
  8. customcondensed
  9. customAs a result crystals were formed
  10. customwhich were recrystallized twice from ether

Sources & evidence

ORD record
ord-ea1fad422f424c9cbbaeb0564efd0ab2
Source dataset
uspto-grants-1977_04
Patent number
US04018824

Reaction notes

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