Phenol → 1-Phenoxy-2-benzyloxy-3-(iso-propylamino)-propane

HRID 2198844Notes

Reaction equation

[CH:1]([N:4]1[CH2:7][CH:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5]1)([CH3:3])[CH3:2].[C:16]1([OH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[K+]>CCOCC>[O:22]([CH2:5][CH:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:7][NH:4][CH:1]([CH3:2])[CH3:3])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 180 °C

Procedure

To a mixture of 6.2 parts of 1-(iso-propyl)-3-benzyloxyazetidine and 28 parts of phenol 1.5 parts of potassium hydroxide was added, and the mixture was heated at 180° C. for 6 hours. The reaction mixture was cooled and 100 parts of ether were added thereto. The excessive phenol was extracted with 2 N-sodium hydroxide aqueous solution and removed. The remaining ether layer was washed in water and dried over anhydrous sodium sulfate. After distillation of ether, the residue was successively subjected to distillation to yield 7.6 parts of 1-phenoxy-2-benzyloxy-3-(iso-propylamino)-propane boiling at 158°-160° C. under 2 mm Hg. The yield was 85%. Results of infra-red spectrum analysis and nuclear magnetic resonance analysis of the product are as follows:

Workup

additionwas added
temperatureThe reaction mixture was cooled
extractionThe excessive phenol was extracted with 2 N-sodium hydroxide aqueous solution
customremoved
washThe remaining ether layer was washed in water
dry with materialdried over anhydrous sodium sulfate
distillationAfter distillation of ether
distillationthe residue was successively subjected to distillation

Sources & evidence

ORD record: ord-7106f3a59eee4af284823fef7fa7af89
Source dataset: uspto-grants-1982_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04360464

Reaction notes

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