Water → 2-Hexadecanoyloxyhexadecanoic acid
Reaction equation
[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:3]([OH:5])=[O:4].[OH2:20]>C(Cl)(=O)CCCCCCCCCCCCCCC>[C:19]([O:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:3]([OH:5])=[O:4])(=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:2][CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
α-Hydroxypalmiticacid (3.2 g) was dissolved in pridine (15 ml), and palmitoyl chloride (3.3 g) was added thereto under stirring at 0° C. The resulting mixture was allowed to stand over night at room temperature. The reaction mixtue was poured into water and the aqueous solution was stirred at room temperature for 1 hour, followed by acidification with 1 N hydrochloric acid solution, and extraction with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated to give a residue which was recrystallized from petroleum ether to afford crystals of 2-hexadecanoyloxyhexadecanoic acid (5.4 g). M.p. 55° to 56° C.
Workup
- additionwas added
- waitto stand over night at room temperature
- stirringthe aqueous solution was stirred at room temperature for 1 hour
- extractionfollowed by acidification with 1 N hydrochloric acid solution, and extraction with ethyl acetate
- washThe extract was washed with water
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customto give a residue which
- customwas recrystallized from petroleum ether
Sources & evidence
- ORD record
- ord-7172565f227e47fa9a3fbb1bf94e9d4b
- Source dataset
- uspto-grants-1984_03
- Patent number
- US04436726
Reaction notes
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