Hydrochloric Acid → HCID 18690412, compound
Reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](Cl)=[O:7].[CH2:9]([Mg]Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl>C1COCC1.[Cu]Cl>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](=[O:7])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -20 °C
Procedure
10 g of 5-chlorovaleroyl chloride in 50 ml of anhydrous THF is loaded into a 250 ml three-necked flask, under a nitrogen atmosphere. The reaction medium is cooled down to -20° C. and 1.06 g of copper (I) chloride is added. Agitation is carried out for 40 minutes, then 36 ml of a 2 M solution of benzylmagnesium chloride in THF is added over 1.5 hour. Agitation is carried out for 1 hour at -20° C., then the temperature is allowed to return to 20° C. over 1.5 hour. The reaction medium is cooled down to -10° C. and 90 ml of 0.4 M hydrochloric acid is added. Agitation is carried out for 20 minutes, then the aqueous phase is extracted twice with 100 ml of MTBE. The organic phase is washed twice with 50 ml of water, dried over magnesium sulphate, filtered and concentrated. In this way, 13.5 g of sought product is obtained.
Workup
- waitAgitation is carried out for 1 hour at -20° C.
- waitto return to 20° C. over 1.5 hour
- temperatureThe reaction medium is cooled down to -10° C.
- waitAgitation is carried out for 20 minutes
- extractionthe aqueous phase is extracted twice with 100 ml of MTBE
- washThe organic phase is washed twice with 50 ml of water
- dry with materialdried over magnesium sulphate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-25dad12673a846f0a2fbd76411378a98
- Source dataset
- uspto-grants-2000_08
- Patent number
- US06107495
Reaction notes
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