Hydrochloric Acid → HCID 12363914, compound

HRID 328907Notes

Reaction equation

HRID 328907 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[C:9]([N:13]1[CH2:16][CH:15]([OH:17])[CH2:14]1)([CH3:12])([CH3:11])[CH3:10].[OH-].[K+].[ClH:20]>>[ClH:20].[OH:2][C:1]1[CH:8]=[CH:7][C:5]([O:6][CH2:16][CH:15]([OH:17])[CH2:14][NH:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 785HydroquinoneHCID 14797Potassium HydroxideHCID 2879861-tert-Butyl-3-hydroxyazetidine

Product 1

HCID 12363914HCID 12363914, compoundYield 58%

Conditions

Temperature
140 °C

Procedure

A mixture of 11 parts of hydroquinone, 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 mixture was cooled and dissolved into 50 parts of 4N-hydrochloric acid aqueous solution. The resulting solution was washed with 50 parts of chloroform. The water layer was acidified with concentrated hydrochloric acid, evaporated and solidified. The residue was dissolved in isopropyl alcohol and filtered. The filtrate was decolored with active carbon and allowed to cool. As a result 6.9 parts of 1-(p-hydroxyphenoxy)-3-(tert.-butylamino)-2-propanol hydrochloride melting at 201° - 203° C were obtained. The yield was 58%. The results of infra-red spectrum analysis and nuclear magnetic resonance analysis of the resulting hydrochloride are as follows:

Workup

  1. temperatureThe reaction mixture was cooled
  2. washThe resulting solution was washed with 50 parts of chloroform
  3. customevaporated
  4. dissolutionThe residue was dissolved in isopropyl alcohol
  5. filtrationfiltered
  6. temperatureto cool

Sources & evidence

ORD record
ord-61c3b1a26efd49f291e3f2502cc15091
Source dataset
uspto-grants-1977_04
Patent number
US04018824

Reaction notes

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