Hydrochloric Acid → HCID 10125490, compound

HRID 1738586Notes

Reaction equation

HRID 1738586 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16].Cl>O.O1CCOCC1>[CH3:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([C:15]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:16])[C:1]=1[OH:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 660858-Aminooctanoic acid

Product 1

HCID 10125490HCID 10125490, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
90 °C

Procedure

A 50% (by weight) solution of potassium carbonate (24 mL, 36 g, 0.127 mol, 1.23 eq), 8-aminocaprylic acid (16.44 g, 0.103 mol, 1.00 eq), and water (20 mL) were added to a 250 mL round bottom flask equipped with a magnetic stir bar and an addition funnel. The white cloudy mixture was treated with a solution of oligo(3-methylsalicylate) (15.90 g, 0.114 mmol 1.11 eq) and dioxane (90 mL), added over five minutes. The addition funnel was replaced with a condenser, and the reaction mixture was heated to 90 degrees C. for 4 hours (at which time the reaction was determined to have finished, by HPLC). The clear orange reaction mixture was cooled to 40 degrees C. and acidified to pH=1 with 3% (by vol.) aqueous hydrochloric acid. All the dioxane and some of the water were stripped (60 degrees C., 50 mm). The water layer from the resulting two-phase mixture was decanted while still warm. The orange oil was crystallized from 65% ethanol-water to give a tan solid upon cooling to -10 degrees C. The solid was recrystallized from 50 mL of 65% ethanol-water. The off-white solid was washed with hot water (30 mL) to remove most of the remaining salicylic acid. The solid was recovered by filtration and was dried over 6 hours in a 50 degrees C. vacuum oven. The N-(3-methylsalicyloyl)-8-aminocaprylic acid was isolated as a light tan solid (12.32 g, 41%).

Workup

  1. customequipped with a magnetic stir bar and an addition funnel
  2. additionadded over five minutes
  3. customThe addition funnel was replaced with a condenser
  4. temperatureThe clear orange reaction mixture was cooled to 40 degrees C
  5. custom(60 degrees C., 50 mm)
  6. customThe water layer from the resulting two-phase mixture was decanted
  7. temperaturewhile still warm
  8. customThe orange oil was crystallized from 65% ethanol-water
  9. customto give a tan solid
  10. temperatureupon cooling to -10 degrees C
  11. customThe solid was recrystallized from 50 mL of 65% ethanol-water
  12. washThe off-white solid was washed with hot water (30 mL)
  13. customto remove most of the remaining salicylic acid
  14. filtrationThe solid was recovered by filtration
  15. customwas dried over 6 hours in a 50 degrees C

Sources & evidence

ORD record
ord-de54110d16ef401995dfef2aa2172a0a
Source dataset
uspto-grants-1999_10
Patent number
US05962710

Reaction notes

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