Mesitylene → 2-(4-Phenoxyphenoxy)ethanamine

HRID 518947Notes

Reaction equation

HRID 518947 reaction equation
C1(C)C=C(C)C=C(C)C=1.[O:10]([C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C[O-].[K+].O1[CH2:31][CH2:30][NH:29]C1=O>>[O:10]([C:17]1[CH:18]=[CH:19][C:20]([O:23][CH2:31][CH2:30][NH2:29])=[CH:21][CH:22]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 4

HCID 7947MesityleneHCID 132544-PhenoxyphenolHCID 739492-OxazolidinoneHCID 23664618Potassium methoxide

Product 1

HCID 110316512-(4-Phenoxyphenoxy)ethanamineYield 45%

Procedure

Mesitylene (24 mL) was added into a round bottom flask containing 4-phenoxyphenol (5.00 g, 26.85 mmol). Potassium methoxide (25% in methanol) (0.79 mL, 2.685 mmol) was added and stirred for 15 minutes. 2-oxazolidinone (2.34 g, 26.85 mmol) was then added, and the reaction mixture was heated to reflux temperature and stirred for 16 h. After cooling the reaction mixture to room temperature, the reaction mixture was filtered over Celite® and the solvent evaporated under reduced pressure. The crude reaction product was isolated by flash column chromatography to yield 2.75 g (45%) of the amine. 1H NMR (MeOD, 400 MHz) δ 8.21-8.11 (m, 2H), 8.35-7.91 (m, 1H), 7.83-7.67 (m, 6H), 7.02-6.96 (m, 2H), 4.71 (dd, 2H, J=5.9, 5.9 Hz), 3.68 (dd, 2H, J=5.8, 5.8 Hz).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux temperature
  3. stirringstirred for 16 h
  4. filtrationthe reaction mixture was filtered over Celite®
  5. customthe solvent evaporated under reduced pressure
  6. customThe crude reaction product
  7. customwas isolated by flash column chromatography

Sources & evidence

ORD record
ord-6b7c5480e4114b39b506cc4e2b45c316
Source dataset
uspto-grants-2015_08
Patent number
US09115237B2

Reaction notes

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