Sodium Carbonate → Decanoic Acid
Reaction equation
C1C=CC2OC(=O)NC(=O)C=2C=1.C([O:15][C:16](=[O:32])[CH:17]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]Br)C(OCC)=O)C.C(=O)([O-])[O-].[Na+].[Na+]>CC(N(C)C)=O>[C:16]([OH:32])(=[O:15])[CH2:17][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
20 g (0.123 mole) carsalam (available from Sigma-Aldrich of Shiboygan Falls, Wis.), 43.16g (0.123 mole) 2-(8-bromooctyl)malonic acid diethyl ester (available from Allied Signal, Inc. of Morristown, N.J.), 15.52 g (0.137 mole) sodium carbonate (available from Sigma-Aldrich of St. Louis, Mo.) and 100 mL dimethylacetamide (DMA) (available from Sigma-Aldrich) were heated to about 75° C. for about 5 hours. The solids were filtered off and the filtrate was stirred in 2N sodium hydroxide at 45° C. for a total of about 9 hours to form N-(2-hydroxybenzoyl)-10-amino)-decanoic acid. Formation of the decanoic acid was evident. It was then heated to about 100° C. to determine if the decanoic acid was indeed forming. HPLC of the reaction showed the 9.09 peak transforms to 8.79, 7.23, 5.78 min. Last HPLC showed 49.6 area % of peak 5.78 min, indicating formation of about 50% (w/w) of the decanoic acid.
Workup
- filtrationThe solids were filtered off
Sources & evidence
- ORD record
- ord-3daf1528ba2e45c8bcc76d0b926326de
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07169776B2
Reaction notes
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