Potassium Carbonate → (3-((8-(1,3-Dioxolan-2-yl)octyl)oxy)-4-methylphenyl)methanol
Reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:10])=[C:7]([OH:9])[CH:8]=1.Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]1[O:24][CH2:23][CH2:22][O:21]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[O:21]1[CH2:22][CH2:23][O:24][CH:20]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][O:9][C:7]1[CH:8]=[C:3]([CH2:2][OH:1])[CH:4]=[CH:5][C:6]=1[CH3:10]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To a stirred solution of 5-(hydroxymethyl)-2-methylphenol (0.57 g, 4.15 mmol) in dimethyl formamide (15 mL), was added 2-(8-bromooctyl)-1,3-dioxolane (1.00 g, 3.77 mmol) and potassium carbonate (0.63 g, 4.57 mmol), and the mixture was stirred at 80° C. for 16 hours. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate (×3). The combined organic extracts were washed with brine, dried (magnesium sulphate), filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 0-7% ethyl acetate in iso-hexane to afford the title compound (0.5 g, 41%).
Workup
- temperatureThe reaction mixture was cooled to room temperature
- extractionextracted with ethyl acetate (×3)
- washThe combined organic extracts were washed with brine
- dry with materialdried (magnesium sulphate)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude material was purified by silica gel chromatography
- washeluting with 0-7% ethyl acetate in iso-hexane
Sources & evidence
- ORD record
- ord-2a390853a79644c2b21b48501b8ef6c7
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877774B2
Reaction notes
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