Ethanol → Ethyl 4-hydroxyhydrocinnamate
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[CH2:13](O)[CH3:14]>Cl>[CH2:13]([O:11][C:10](=[O:12])[CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[CH3:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 145 °C
Procedure
4 drops of concentrated HCl are added, under stirring, to a solution of commercial 3-(4 Hydroxy-phenyl)-propionic acid (13.08 g; 78.79 mmol) in 100 mL of ethanol. The reaction medium is heated to reflux in a bath at 145° C. overnight. The ethanol is evaporated off and ethyl acetate is added. The organic phase is washed with a saturated NaHCO3 solution and with a NaCl solution. After drying over MgSO4 and evaporation, an oil is obtained. This latter is distilled by Kugelrohr (150-175° C.; 1.2 mmbar). A transparent oil which crystallizes is obtained in order to produce the expected compound 4′-1 (13.8 g; 71.1 mmol; 90%) in the form of a white solid.
Workup
- temperatureThe reaction medium is heated
- customThe ethanol is evaporated off
- additionethyl acetate is added
- washThe organic phase is washed with a saturated NaHCO3 solution and with a NaCl solution
- dry with materialAfter drying over MgSO4 and evaporation
- customan oil is obtained
- distillationThis latter is distilled by Kugelrohr (150-175° C.; 1.2 mmbar)
- customA transparent oil which crystallizes
- customis obtained in order
Sources & evidence
- ORD record
- ord-4e8023f51d4c4787be217bba9c8cbfb1
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08389569B2
Reaction notes
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