Gamma-undecalactone → 4-Hydroxy-undecanoic acid dodecylamide
Reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([NH2:17])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH3:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]1[O:30][C:28](=[O:29])[CH2:27][CH2:26]1>C(Cl)Cl>[CH2:5]([NH:17][C:28](=[O:29])[CH2:27][CH2:26][CH:25]([OH:30])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH3:18])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 19.0 g aluminum chloride, dissolved in methylene chloride, was cooled to 0° C. and 46.5 g dodecylamine in methylene chloride was added dropwise (exothermic). At room temperature, 19.3 g gamma-undecalactone was added rapidly. The temperature rose to 36° C. The reaction was stirred at room temperature for 4 hours. The mixture was quenched with water and filtered over Celite. The liquid was extracted with ether and washed with water and brine. The solution was dried, filtered and evaporated to dryness. The resulting brown crystals were purified by recrystallization from ether/ethylacetate to give pale yellow crystals.
Workup
- customrose to 36° C
- customThe mixture was quenched with water
- filtrationfiltered over Celite
- extractionThe liquid was extracted with ether
- washwashed with water and brine
- customThe solution was dried
- filtrationfiltered
- customevaporated to dryness
- customThe resulting brown crystals were purified by recrystallization from ether/ethylacetate
- customto give pale yellow crystals
Sources & evidence
- ORD record
- ord-491a19afb3174b878e9a949db83ba780
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06437150B1
Reaction notes
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