5-Chloro-2,3-dimethoxybenzaldehyde → 1-(5-Chloro-2,3-dimethoxyphenyl)ethanol
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:14][Mg]Br>C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10][CH3:11])=[C:6]([CH:7]([OH:8])[CH3:14])[CH:9]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 5-chloro-2,3-dimethoxy-benzaldehyde (7.0 g, 34.90 mmol) in dry diethyl ether (500 mL) at 0° C. was added methylmagnesium bromide of 3.0 M in diethyl ether (29 mL, 87.22 mmol). The reaction mixture was brought to room temperature and stirred for 30 min; refluxed for 3 h; then cooled to 0° C. and quenched by adding saturated aqueous NH4Cl. The two liquid layers were separated. The aqueous layer was extracted with diethyl ether. The combined organic layers were washed with water, dried, and concentrated to the crude compound which was purified by silica gel column (10-25% ethyl acetate in hexanes) to afford 1-(5-chloro-2,3-dimethoxy-phenyl)-ethanol (5.67 g, 75%): 1H NMR (400 MHz, CDCl3): δ 7.00 (d, 1 H), 6.81 (d, 1 H), 5.11 (m, 1 H), 3.86 (s, 6 H), 2.30 (d, 1 H), 1.48 (d, 3 H).
Workup
- customwas brought to room temperature
- temperaturerefluxed for 3 h
- customquenched
- additionby adding saturated aqueous NH4Cl
- customThe two liquid layers were separated
- extractionThe aqueous layer was extracted with diethyl ether
- washThe combined organic layers were washed with water
- customdried
- concentrationconcentrated to the crude compound which
- customwas purified by silica gel column (10-25% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-ecdf62a3bd264499b0564affada312f0
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08604021B2
Reaction notes
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