Phenyl glycidyl ether → HCID 22154115, compound

HRID 1651124Notes

Reaction equation

HRID 1651124 reaction equation
[ClH:1].[NH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[O:13]1[CH:15]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14]1>>[ClH:1].[OH:13][CH:15]([CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:14][NH:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 31217Phenyl glycidyl etherHCID 221541064-(2-Aminoethoxy)phenol--hydrogen chloride (1/1)

Product 1

HCID 22154115HCID 22154115, compoundYield 15.6%

Procedure

A mixture of p-(2-aminoethoxy)phenol hydrochloride (1.89 g) triethylamine (1.01 g) and 1,2-epoxy-3-phenoxypropane (1.5 g) was heated under reflux for 24 hours. The reaction mixture was cooled and the solvent was evaporated. The residue was partitioned between dichloromethane (100 ml) and 10% w/v potassium carbonate solution. The organic layer was separated, dried (MgSO4), and the solvent was evaporated. The residual oil was dissolved in ethyl acetate and dry hydrogen chloride was passed through the solution until no further solid precipitated. The precipitate was collected and recrystallised from methanol and ethyl acetate to give p-(2-[2-hydroxy-3-phenoxypropylamino]-ethoxy)phenol hydrochloride (0.53 g), mp, 171°-72° C.; microanalysis: found C,60.3; H,6.7; N,4.0; Cl, 10.6%; required for C17H22NClO4 : C,60.1; H,6.5; N,4.1; Cl,10.5%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent was evaporated
  5. customThe residue was partitioned between dichloromethane (100 ml) and 10%
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. customthe solvent was evaporated
  9. dissolutionThe residual oil was dissolved in ethyl acetate
  10. customprecipitated
  11. customThe precipitate was collected
  12. customrecrystallised from methanol and ethyl acetate

Sources & evidence

ORD record
ord-46c2bb2e68d2435d8660f34f2cf61b23
Source dataset
uspto-grants-1990_05
Patent number
US04927836

Reaction notes

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