4-Hydroxybenzyl Alcohol → HCID 58047044, compound
Reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH:18]1[CH2:21][CH2:20][CH2:19]1.O>C(O)C>[CH:18]1([CH2:17][O:9][C:6]2[CH:7]=[CH:8][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=2)[CH2:21][CH2:20][CH2:19]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 4-(hydroxymethyl)phenol (3.20 g, 25.8 mmol), potassium carbonate (7.12 g, 51.6 mmol) and (bromomethyl)cyclobutane (3.75 mL, 33.6 mmol) in ethanol (50 mL) was stirred at 70° C. overnight. Water was added thereto, ethanol was evaporated under reduced pressure, and the mixture was extracted twice with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=19:1 to 13:7), and then purified by basic silica gel chromatography (hexane:ethyl acetate=19:1 to 13:7), and the solvent was evaporated to give the title compound (1.17 g, yield 23%) as an oil.
Workup
- customethanol was evaporated under reduced pressure
- extractionthe mixture was extracted twice with ethyl acetate
- washThe combined organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=19:1 to 13:7)
- custompurified by basic silica gel chromatography (hexane:ethyl acetate=19:1 to 13:7)
- customthe solvent was evaporated
Sources & evidence
- ORD record
- ord-cfc51b9c36db4257bfbe001df30462d7
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501804B2
Reaction notes
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