Phenol → HCID 13055710, compound

HRID 2198846Notes

Reaction equation

HRID 2198846 reaction equation
[CH:1]([N:4]1[CH2:7][CH:6]([O:8][CH2:9][O:10][CH3:11])[CH2:5]1)([CH3:3])[CH3:2].[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+]>CCOCC>[O:18]([CH2:5][CH:6]([O:8][CH2:9][O:10][CH3:11])[CH2:7][NH:4][CH:1]([CH3:2])[CH3:3])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 14798Sodium HydroxideHCID 205173143-(Methoxymethoxy)-1-(propan-2-yl)azetidine

Product 1

HCID 13055710HCID 13055710, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
180 °C

Procedure

To a mixture of 1.6 parts of 1-iso-propyl-3-methoxymethoxyazetidine and 9.4 parts of phenol 0.5 part of sodium hydroxide was addded, and the mixture was heated at 180° C. for 6 hours. The reaction mixture was cooled and 100 parts of ether were added thereto. Excessive phenol was removed by extraction with 2 N-sodium hydroxide aqueous solution, and the remaining ether layer was washed in water and dried over anhydrous sodium sulfate. After distillation of ether, the residue was subjected to distillation to yield 1.6 parts of 1-phenoxy-2-methoxymethoxy-3-(iso-propylamino)-propane boiling at 146°-149° C. under 2 mm Hg. The yield was 67%.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customExcessive phenol was removed by extraction with 2 N-sodium hydroxide aqueous solution
  3. washthe remaining ether layer was washed in water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationAfter distillation of ether
  6. distillationthe residue was subjected to distillation

Sources & evidence

ORD record
ord-2c1f4e08a2ae4f29958bfbdb7772391f
Source dataset
uspto-grants-1982_11
Patent number
US04360464

Reaction notes

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