Potassium Iodide → HCID 58947033, compound

HRID 2369465Notes

Reaction equation

HRID 2369465 reaction equation
C[C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]([C:11](O)=[O:12])=[C:4](C)[C:3]=1[OH:15].[C:16](=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40].CN([CH:44]=[O:45])C>>[CH2:25]([O:15][C:3]1[CH:4]=[C:5]([C:11]([O:45][CH3:44])=[O:12])[CH:6]=[C:7]([CH:2]=1)[C:8]([O:10][CH3:16])=[O:9])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 82131-BromohexadecaneHCID 11430Potassium CarbonateHCID 129858547HCID 129858547, compound

Product 1

HCID 58947033HCID 58947033, compound

Conditions

Temperature
60 °C

Procedure

A 100 mL round bottom flask is charged with dimethyl-5-hydroxyisophthalic acid (0.2584 g, 1.23 mmol), potassium carbonate (0.356 g, 2.58 mmol), and potassium iodide (0.2018 g, 1.22 mmol) under an inert atmosphere. Anhydrous N,N′-dimethylformamide (10 mL) is added and the mixture is heated to 60° C. for 2 h. Bromohexadecane (0.376 mL, 1.23 mmol) is then added and the reaction is stirred overnight. After cooling to room temperature the reaction is concentrated by rotary evaporation. The crude solid is suspended in diethyl ether (40 mL), and is successively washed with deionized water (20 mL), citric acid (5 wt %, 20 mL), deionized water (20 mL), and brine (20 mL). The ether layer is separated, filtered through glass wool, concentrated by rotary evaporation, and dried in vacuo to yield and off-white solid (0.53 g, 100%).

Workup

  1. temperatureAfter cooling to room temperature the reaction
  2. concentrationis concentrated by rotary evaporation
  3. washis successively washed with deionized water (20 mL), citric acid (5 wt %, 20 mL), deionized water (20 mL), and brine (20 mL)
  4. customThe ether layer is separated
  5. filtrationfiltered through glass wool
  6. concentrationconcentrated by rotary evaporation
  7. customdried in vacuo
  8. customto yield

Sources & evidence

ORD record
ord-e722ab6917404f76a4d7a5a5e0fbe82d
Source dataset
uspto-grants-2014_04
Patent number
US08703988B2

Reaction notes

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