| Identification | Back Directory | [Name]
2-(4-Methoxybenzyloxy)ethanol | [CAS]
13807-89-1 | [Synonyms]
2-(4-Methoxybenzyloxy)ethanol
2-[(4-methoxyphenyl)methoxy]ethanol
Ethanol, 2-[(4-methoxyphenyl)methoxy]- | [Molecular Formula]
C10H14O3 | [MDL Number]
MFCD12756484 | [MOL File]
13807-89-1.mol | [Molecular Weight]
182.22 |
| Chemical Properties | Back Directory | [Boiling point ]
144 °C(Press: 4 Torr) | [density ]
1.093±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [pka]
14.36±0.10(Predicted) | [Appearance]
yellow oil |
| Hazard Information | Back Directory | [Synthesis]
The general procedure for the synthesis of 2-(4-methoxybenzyloxy)ethanol from ethylene glycol and 1-(chloromethyl)-4-methoxybenzene was as follows: potassium hydroxide (1.07 g, 19 mmol) was mixed with ethylene glycol (11 mL, 19 mmol), and the mixture was heated and stirred for 3 hours at 130 °C. Upon completion of the reaction, the mixture was cooled to room temperature, followed by the addition of 1-(chloromethyl)-4-methoxybenzene (3 g, 19 mmol). The reaction system was heated up to 350 °C under nitrogen protection for 16 hours. At the end of the reaction, water and ethyl acetate (EtOAc) were added to the system and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure. Purification was carried out by column chromatography (Redisep column), using ethyl acetate/cyclohexane as eluent, to give 2-(4-methoxybenzyloxy)ethanol as an oil. Yield: 2.26 g (66% yield).LC-MS (Method 2): retention time (Rt) 2.34 min, no molecular ion peak observed. | [References]
[1] Tetrahedron Letters, 2009, vol. 50, # 19, p. 2270 - 2273
[2] Angewandte Chemie - International Edition, 2009, vol. 48, # 49, p. 9346 - 9349
[3] Organic Letters, 2010, vol. 12, # 2, p. 384 - 387
[4] Chemistry - A European Journal, 2010, vol. 16, # 31, p. 9457 - 9461
[5] Journal of the American Chemical Society, 2016, vol. 138, # 7, p. 2190 - 2193 |
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