Potassium Carbonate → Phenol

HRID 2097359Notes

Reaction equation

[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.BrCCCCCC[N:24]1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=O.[C:35]([O-:38])([O-])=O.[K+].[K+]>CN(C=O)C>[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:12][CH2:11][CH2:10][CH2:15][CH2:14][CH2:25][C:26]34[CH:33]=[CH:32][CH:31]=[CH:30][CH:27]3[C:28]([NH:24][C:35]4=[O:38])=[O:29])=[CH:12][CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:10]1([OH:9])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 95 °C

Procedure

4-(2-Morpholin-4-yl-ethoxy)-phenol (3.39 g, 15.2 mmol), N-(6-bromohexyl)-phthalimide (4.72 g, 15.2 mmol) and K2CO3 (4.20 g, 30.4 mmol) were suspended in DMF (35 mL) under an atmosphere of argon and stirred at 95° C. for 17 h. The solvent was evaporated under reduced pressure and the residue was partitioned between water (150 mL) and CH2Cl2 (150 mL). The aqueous layer was extracted with CH2Cl2 (2×100 mL), the combined org. layers were dried over Na2SO4, filtered and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (EtOAc) to give the title compound together with some starting phenol (≈2:1). The mixture was used for subsequent reactions without further purification.

Workup

customThe solvent was evaporated under reduced pressure
customthe residue was partitioned between water (150 mL) and CH2Cl2 (150 mL)
extractionThe aqueous layer was extracted with CH2Cl2 (2×100 mL)
dry with materiallayers were dried over Na2SO4
filtrationfiltered
customthe solvent was removed under reduced pressure
customThe residue was purified by flash chromatography (EtOAc)

Sources & evidence

ORD record: ord-d572a98e356e4b239b2089837fc82438
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450348B2

Reaction notes

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