Hydrochloric Acid → HCID 19778816, compound
Reaction equation
[CH2:1]([C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15](O)=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].S(Cl)([Cl:24])=O.C([Li])CCC.Cl>C(Cl)Cl>[CH2:1]([C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([Cl:24])=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
2-Dodecylbenzoyl chloride was prepared from 2-dodecylbenzoic acid (4.06 g, 14 mmoles) and excess thionyl chloride in methylene chloride at 23° C. for 1 hour. Following evaporation of the solvents, the acid chloride was used without purification. A solution of this acid chloride in tetrahydrofuran (15 ml) was added to the cold solution of dianion prepared above, followed by an additional amount of 2.12M n-butyl lithium (6.6 ml). The solution was warmed to -20° C., stirred for 1 hour and poured into cold 1N hydrochloric acid. The mixture was extracted with diethyl ether. The extracts were washed with water, dried and evaporated. The crude product was recrystallized from acetonitrile.
Workup
- customevaporation of the solvents
- customthe acid chloride was used without purification
- additionA solution of this acid chloride in tetrahydrofuran (15 ml) was added to the cold solution of dianion
- customprepared above,
- extractionThe mixture was extracted with diethyl ether
- washThe extracts were washed with water
- customdried
- customevaporated
- customThe crude product was recrystallized from acetonitrile
Sources & evidence
- ORD record
- ord-6991306a5e094153bd627c5d6c26baab
- Source dataset
- uspto-grants-1993_02
- Patent number
- US05189226
Reaction notes
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