HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Potassium Hydroxide → 1-(2',3'-Dimethyl-4'-methoxyphenoxy)-3-(tert.-butylamino)-2-propanol

HRID 328908
Notes
Print preview

Reaction equation

HRID 328908 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[OH:11].[C:12]([N:16]1[CH2:19][CH:18]([OH:20])[CH2:17]1)([CH3:15])([CH3:14])[CH3:13].[OH-].[K+]>Cl>[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[O:11][CH2:17][CH:18]([OH:20])[CH2:19][NH:16][C:12]([CH3:13])([CH3:14])[CH3:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 2879861-tert-Butyl-3-hydroxyazetidineHCID 109316254-Methoxy-2,3-dimethylphenol

Product 1

HCID 130557041-(2',3'-Dimethyl-4'-methoxyphenoxy)-3-(tert.-butylamino)-2-propanolYield 72.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 9.1 parts of 2,3-dimethyl-4-methoxyphenol, 6.5 parts of 1-(tert.-butyl)-3-azetidinol and 0.3 part of potassium hydroxide was heated under nitrogen gas at 140° C. for 8 hours with agitation. The reaction product was dissolved in 100 parts of 2N-hydrochloric acid aqueous solution and washed twice with 100 parts of ether. The water layer was made alkaline with 4N-sodium hydroxide aqueous solution, and the resulting crystals were recovered by filtration and dried. Then the crystals were dissolved in 100 parts of ether and decolored. The decolored liquid was concentrated and allowed to cool. As a result 10.2 parts of 1-(2',3'-dimethyl-4'-methoxyphenoxy)-3-(tert.-butylamino)-2-propanol melting at 73° - 75° C were obtained. The yield was 72.5%. The results of infra-red spectrum analysis and nuclear magnetic resonance analysis of the product are as follows:

Workup

  1. washwashed twice with 100 parts of ether
  2. filtrationthe resulting crystals were recovered by filtration
  3. customdried
  4. dissolutionThen the crystals were dissolved in 100 parts of ether
  5. concentrationThe decolored liquid was concentrated
  6. temperatureto cool

Sources & evidence

ORD record
ord-911a95107cd543e8925d5af305b8bf8b
Source dataset
uspto-grants-1977_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04018824

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes