Hydrochloric Acid → 1,3-Propanediyl disalicylate

HRID 1444615Notes

Reaction equation

HRID 1444615 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].Br[CH2:12][CH2:13][CH2:14]Br.[OH2:16].Cl>CN(C=O)C>[C:1]([O:10][CH2:12][CH2:13][CH2:14][O:16][C:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 338Salicylic AcidHCID 962WaterHCID 80011,3-Dibromopropane2×

Product 1

HCID 75035871,3-Propanediyl disalicylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

13.94 ml TEA (100 mmol) were added to a solution of 13.81 g salicylic acid (SA; 100 mmol) in 40 ml DMF at 60° C., the reaction mixture was stirred for 20 minutes at 60° C., and 12.2 g 1,3-dibromo propane (Compound 18d; 50 mmol) were added. The reaction mixture was stirred at 60° C. for 24 hours, cooled to room temperature, poured into 250 ml cold water, and acidified to about pH 4 with 1N HCl. A white precipitate separated. The precipitate was filtered, washed with water, and dried in a vacuum oven at 40° C. overnight. The thus obtained crude product was recrystallized from n-heptane to obtain a pure product.

Workup

  1. stirringThe reaction mixture was stirred at 60° C. for 24 hours
  2. temperaturecooled to room temperature
  3. customA white precipitate separated
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. customdried in a vacuum oven at 40° C. overnight
  7. customThe thus obtained crude product
  8. customwas recrystallized from n-heptane
  9. customto obtain a pure product

Sources & evidence

ORD record
ord-c44d9dff53934e89a2f1c840f4c29707
Source dataset
uspto-grants-2010_02
Patent number
US07662864B2

Reaction notes

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