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

HRID 328908Notes

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]

Participants

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

washwashed twice with 100 parts of ether
filtrationthe resulting crystals were recovered by filtration
customdried
dissolutionThen the crystals were dissolved in 100 parts of ether
concentrationThe decolored liquid was concentrated
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

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