Iodoethane → 3-Ethoxy-5-(hydroxymethyl)phenol
Reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([OH:10])[CH:6]=[C:7]([OH:9])[CH:8]=1.C([O-])([O-])=O.[K+].[K+].[CH2:17](I)[CH3:18]>CN(C=O)C>[CH2:17]([O:9][C:7]1[CH:6]=[C:5]([OH:10])[CH:4]=[C:3]([CH2:2][OH:1])[CH:8]=1)[CH3:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 5-hydroxymethyl-benzene-1,3-diol (0.5 g, 3.57 mmol, 1.0 equiv) in DMF (5 mL) was added K2CO3 (0.99 g, 7.14 mmol, 2.0 equiv) and ethyl iodide (0.29 mL, 0.43 g, 3.93 mmol, 1.1 equiv) and the reaction mixture stirred under Ar at 60° C. for 4 h. The K2CO3 was removed by filtration, the filtrate extracted with ethyl acetate (3×50 mL), the combined organic phases washed with a sat. solution of sodium chloride (1×50 ml) and dried over Na2SO4. The solvent was removed by evaporation under reduced pressure and the crude material purified with column chromatography on silica eluting with a gradient of hexane/ethyl acetate (4:1→2:1) providing 0.25 g (42%) of the title compound. 1H NMR (250 MHz, CDCl3): δ 1.40 (t, J=7.0 Hz, 3H), 4.02 (q, J=7.0 Hz, 2H), 4.61 (d, J=5.6 Hz, 2H), 4.91 (br s, 1H), 6.29-6.31 (m, 1H), 6.43 (br s, 1H), 6.49 (br s, 1H). MS (EI): 168.0 [M]+.
Workup
- customThe K2CO3 was removed by filtration
- extractionthe filtrate extracted with ethyl acetate (3×50 mL)
- washthe combined organic phases washed with a sat. solution of sodium chloride (1×50 ml)
- dry with materialdried over Na2SO4
- customThe solvent was removed by evaporation under reduced pressure
- customthe crude material purified with column chromatography on silica eluting with a gradient of hexane/ethyl acetate (4:1→2:1)
Sources & evidence
- ORD record
- ord-e9b05f10b5874f5ca7fb77473efb4736
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07645753B2
Reaction notes
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