Hydrochloric Acid → HCID 24771977, compound
Reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([OH:10])[CH:9]=1)=[O:3].Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19]CC)=[O:18].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].Cl>C(O)C>[C:2]([C:4]1[CH:9]=[C:8]([CH:7]=[CH:6][CH:5]=1)[O:10][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])(=[O:3])[CH3:1]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A round bottom flask equipped with a magnetic stirrer bar and a reflux condenser was charged with 5.0 g (36.7 mmol) of 3-hydroxyacetophenone, 8.18 g (36.7 mmol) of ethyl 6-bromohexanoate and 50 mL of ethanol. The clear reaction mixture was treated with potassium carbonate (6.03 g, 44.0 mmol) and heated to reflux. After stirring for 24 hr at reflux, the reaction mixture was cooled to 25° C., filtered through a Celite pad and concentrated. The residue was taken up in of ethanol and treated with 15 mL of 2N aqueous sodium hydroxide (30 mmol). The reaction mixture was stirred for 6 hr at 25° C., before the ethanol was stripped off. The residue was acidified with aqueous 1N hydrochloric acid. The resulting solid was isolated by filtration and purified by recrystallization from ethanol/water to yield an off-white solid, 7.57 g, mp 70-72° C.
Workup
- customA round bottom flask equipped with a magnetic stirrer bar and a reflux condenser
- temperatureheated to reflux
- temperatureat reflux
- filtrationfiltered through a Celite pad
- concentrationconcentrated
- customThe resulting solid was isolated by filtration
- custompurified by recrystallization from ethanol/water
- customto yield an off-white solid, 7.57 g, mp 70-72° C.
Sources & evidence
- ORD record
- ord-3b79f799df8546b180b2351e5773eafc
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895777B2
Reaction notes
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