2-Chloroethanol → 2-(4-Methoxyphenoxy)ethanol
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.Cl[CH2:11][CH2:12][OH:13].[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:11][CH2:12][OH:13])=[CH:5][CH:4]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 148.8 g (1.20 mole) of p-methoxyphenol, 170.0 g (2.11 mole) of 2-chloroethanol and 47.2 g (1.18 mole) of sodium hydroxide in 1.5 liter of absolute ethanol was heated at reflux for 22 hr. The solution was filtered, and the solvent was removed from the filtrate in vacuo. The residue was crystallized from methylene chloride-hexane to give 71.4 g (35%) of title compound as a white crystalline solid, mp 69°-71° C.
Workup
- temperaturewas heated
- temperatureat reflux for 22 hr
- filtrationThe solution was filtered
- customthe solvent was removed from the filtrate in vacuo
- customThe residue was crystallized from methylene chloride-hexane
Sources & evidence
- ORD record
- ord-f740797ed7e845ebb71bed2ef176384d
- Source dataset
- uspto-grants-1993_03
- Patent number
- US05194446
Reaction notes
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