Diethyl Ether → 2-(3-Methoxyphenyl)-2-propanol
Reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[CH:5]=1)=[O:3].[CH3:12][Mg]I.C(OCC)C>>[CH3:11][O:10][C:6]1[CH:5]=[C:4]([C:2]([OH:3])([CH3:12])[CH3:1])[CH:9]=[CH:8][CH:7]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
A flame-dried 25 mL R.B. flask equipped with a reflux condenser was charged, under argon, with 3-methoxyacetophenone (1 g, 6.66 mmol) at 0° C. Methylmagnesium iodide in diethylether (4.4 mL, 13.3 mmol, 3M) was then added. The reaction mixture was brought to reflux for 60 min and then cool down to 0° C. and quenched with successive addition of water (5 mL) and saturated ammonium chloride (25 mL). The mixture was extracted with diethyl ether (3×20 mL), the organic extracts were washed successively with 20% sodium bisulfite and saturated sodium bicarbonate, dried, filtered and concentrated. Purification by flash chromatography, using 15% acetone in hexanes, yields propan-2-ol (0.832 g, 75%). 1H NMR (400 MHz, acetone-d6) δ: 1.51 (s, 6H), 3.79 (s, 3H), 6.77 (d, 1H, J=8.1 Hz), 7.07 (d, 1H, J=7.7 Hz), 7.13 (s, 1H), 7.22 (t, 1H, J=7.9 Hz).
Workup
- customflask equipped with a reflux condenser
- temperatureto reflux for 60 min
- customquenched with successive addition of water (5 mL) and saturated ammonium chloride (25 mL)
- extractionThe mixture was extracted with diethyl ether (3×20 mL)
- washthe organic extracts were washed successively with 20% sodium bisulfite and saturated sodium bicarbonate
- customdried
- filtrationfiltered
- concentrationconcentrated
- customPurification by flash chromatography
- customyields propan-2-ol (0.832 g, 75%)
Sources & evidence
- ORD record
- ord-6882be85056f462a95e924aa7f15814b
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09090651B2
Reaction notes
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