Hydrochloric Acid → HCID 641053, compound
Reaction equation
[Cl:1][CH2:2][CH2:3][C:4](Cl)=[O:5].[CH2:7]([Mg]Br)[CH:8]=[CH2:9].O.Cl.O1C[CH2:17][CH2:16][CH2:15]1>C(OCC)C>[Cl:1][CH2:2][CH2:3][C:4]([OH:5])([CH2:17][CH:16]=[CH2:15])[CH2:7][CH:8]=[CH2:9]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -15 °C
Procedure
3-Chloro-propionyl chloride (5.00 g) dissolved in tetrahydrofuran (50 mL) is added dropwise to a 1 M solution of allylmagnesium bromide in diethyl ether (72 mL) cooled to −15° C. The solution is warmed in the cooling bath to room temperature over a period of 2 h and stirred at room temperature overnight. Water is then added and the resulting mixture is neutralized using 4 M aqueous hydrochloric acid. The mixture is extracted with diethyl ether (3×) and the combined extracts are washed with water (2×). The organic phase is dried (Na2SO4) and the solvent is evaporated to afford the crude title compound. Yield: 7.87 g (ca. 85% pure).
Workup
- temperatureThe solution is warmed in the cooling bath to room temperature over a period of 2 h
- extractionThe mixture is extracted with diethyl ether (3×)
- washthe combined extracts are washed with water (2×)
- dry with materialThe organic phase is dried (Na2SO4)
- customthe solvent is evaporated
Sources & evidence
- ORD record
- ord-48a1001fcdb84c3ba5712150efe30b58
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765744B2
Reaction notes
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