Hydrochloric Acid → HCID 58788081, compound
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C([O-])([O-])=O.[K+].[K+].Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].Cl>CN(C=O)C>[CH2:20]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH3:20])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
Methyl 3,5-dihydroxybenzoate (4.2 g, 25 mmol) was dissolved in 25 mL of dry DMF and then 13.86 g (100 mmol) of K2CO3 was added in the reaction mixture, where the above mixture was stirred at 80° C. for 1 h under a N2 atmosphere and then 1-bromododecane (12.4 g, 50 mmol) was added dropwise to the reaction mixture. The reaction mixture was stirred at 90° C. for 24 h under N2. At the end of the reaction, the mixture was poured onto ice, 2N—HCl and extracted with MC, H20, NaHCO3 and brine. The solvent was removed in vacuo. The crude solid was purified by column chromatograph with 10% EA and hexane to yield 75% of the product. 1H-NMR (300 MHz, CDCl3) δ 7.1 (d, 2H), 6.6 (t, 1H), 4.0 (t, 4H), 3.9 (s, OCH3), 1.7-1.8 (m, 4H), 1.4-1.6 (m, 4H), 1.1-1.3 (m, 32H), 0.9 (t, 6H).
Workup
- stirringThe reaction mixture was stirred at 90° C. for 24 h under N2
- customAt the end of the reaction
- extractionextracted with MC, H20, NaHCO3 and brine
- customThe solvent was removed in vacuo
- customThe crude solid was purified by column chromatograph with 10% EA and hexane
Sources & evidence
- ORD record
- ord-1503100fd0a140e4b6c166bd9dff28a2
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618298B2
Reaction notes
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