Salicylic Acid → Propyl salicylate

HRID 1259022Notes

Reaction equation

HRID 1259022 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[C:13]([OH:22])(=[O:21])[C:14]1[C:15](=[CH:17][CH:18]=[CH:19][CH:20]=1)[OH:16].[CH2:23](O)[CH2:24][CH3:25].O>CN(C=O)C>[OH:16][C:15]1[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=1[C:13]([O:22][CH2:23][CH2:24][CH3:25])=[O:21]

Participants

6

Reactant 4

HCID 338Salicylic AcidHCID 962WaterHCID 10311-PropanolHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 69092Propyl salicylateYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

CDI (2.34 g, 14.48 mmol) was added to a solution of salicylic acid (2.00 g, 14.48 mmol) in DMF (40 mL). The reaction mixture was stirred at 50° C. for 4 h and PrOH (2.72 mL, 36.20 mmol) was dropwise added. The reaction mixture was stirred at 50° C. for 16 h and allowed to reach r.t. It was poured into H2O (20 mL) and extracted with Et2O (2×40 mL). The organic layer was washed with NaHCO3 (20 mL, saturated aqueous solution), dried over Na2SO4 (anhydrous), filtered and concentrated. The crude residue was flash chromatographed on SiO2 (5% EtOAc/hexanes) to furnish 2.05 g of propyl 2-hydroxybenzoate (colourless oil, yield: 79%).

Workup

  1. stirringThe reaction mixture was stirred at 50° C. for 16 h
  2. customto reach r.t
  3. extractionextracted with Et2O (2×40 mL)
  4. washThe organic layer was washed with NaHCO3 (20 mL, saturated aqueous solution)
  5. dry with materialdried over Na2SO4 (anhydrous)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed on SiO2 (5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-edb30f89a29d4a1da2bfbc05c9c7bc96
Source dataset
uspto-grants-2013_06
Patent number
US08466197B2

Reaction notes

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