Hydrochloric Acid → HCID 67067397, compound
Reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([CH2:7][C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1.C([Li])CCC.Br[CH2:18][CH2:19][CH2:20][Cl:21].Cl>C1COCC1.C(OCC)(=O)C>[Cl:21][CH2:20][CH2:19][CH2:18][CH:7]([C:4]1[CH:3]=[CH:2][C:1]([CH3:11])=[CH:6][CH:5]=1)[C:8]([OH:10])=[O:9]Participants
Conditions
- Temperature
- -78 °C
Procedure
A solution of p-tolylacetic acid (1 g) in THF (30 mL) was stirred at −78° C. for 30 minutes. n-Butyl lithium (2.66 M solution in hexane, 5.01 mL) was added to the solution, and the reaction solution was stirred at −78° C. for three hours. Thereafter, the reaction solution was stirred at 0° C. for 30 minutes, 1-bromo-3-chloropropane (0.725 mL) was added to the reaction solution, and the reaction solution was stirred at room temperature for 24 hours. Thereafter, ethyl acetate and 1 N aqueous hydrochloric acid were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 1.53 g of the title compound. The property values corresponded to the reported values (CAS #2856-76-0).
Workup
- stirringThereafter, the reaction solution was stirred at 0° C. for 30 minutes
- stirringthe reaction solution was stirred at room temperature for 24 hours
- customthe organic layer was separated
- dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-8bd5d084b68846c49fdb18972f889595
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07897632B2
Reaction notes
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