Ethylene Glycol → [2-(benzylamino)phenyl]methanol

HRID 984606Notes

Reaction equation

HRID 984606 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.I[C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20][OH:21].C(O)CO>[Cu]I.CCCCCC.C(OCC)(=O)C.CC(O)C>[CH2:9]([NH:16][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20][OH:21])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 7504BenzylamineHCID 62657Potassium Phosphate, TribasicHCID 1076292-Iodobenzylic alcohol

Product 1

HCID 296053[2-(benzylamino)phenyl]methanolYield 95.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

The general procedure under argon was followed using copper(I) iodide (10 mg, 0.5 mmol), K3PO4 (425 mg, 2.00 mmol), benzylamine (131 μL, 1.20 mmol), 2-iodobenzylalcohol (234 mg, 1.00 mmol), ethylene glycol (111 μL, 2.00 mmol) and 2-propanol (1.0 mL). Column chromatography using a solvent mixture (hexane/ethyl acetate=4/1, Rf=0.3) afforded 2-(N-benzyl)aminobenzylalcohol (203 mg, 95% isolated yield) as off-white solid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity. See Coppola, G. A. J. Herterocyl. Chem. 1986, 23, 223-224.

Sources & evidence

ORD record
ord-0f4c318922074d12be3ea4850804fa00
Source dataset
uspto-grants-2005_03
Patent number
US06867298B2

Reaction notes

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