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

HRID 1883369Notes

Reaction equation

HRID 1883369 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, Rƒ=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-29eb3bb92799474897c4774b75fbb3b6
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

Loading…