Hydrochloric Acid → HCID 5080667, compound

HRID 2229549Notes

Reaction equation

HRID 2229549 reaction equation
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH:12]=[CH2:13])[CH:7]=[CH:6][C:5]=1[OH:14].[OH-].[Na+].Cl>CO>[OH:14][C:5]1[CH:6]=[CH:7][C:8]([O:10][CH2:11][CH2:12][CH3:13])=[CH:9][C:4]=1[C:3]([OH:15])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12870924HCID 12870924, compound

Product 1

HCID 5080667HCID 5080667, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-allyloxy-2-hydroxy-benzoic acid methyl ester (6.10 g, 29.30 mmol) was dissolved in methanol (25.0 mL, 1.2 M) . This solution was treated with aq NaOH (75 mL, 1.33 M, 100 mmol) and stirred at room temperature for 48 h. The reaction is acidified to pH 1-2 with conc. HCl and extracted with ethyl acetate (4×). The combined organic extracts are washed with H2O(2×), aq saturated NaCl, dried with Na2SO4, filtered and concentrated to give 2-hydroxy-5-propoxy-benzoic acid (5.30 g, 91%) as a pale yellow solid: Anal. calcd for C10 H10O4: C, 61.85; H, 5.19. Found: C, 62.06; H, 5.27.

Workup

  1. extractionextracted with ethyl acetate (4×)
  2. washThe combined organic extracts are washed with H2O(2×), aq saturated NaCl
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d280cfb6baec4a71a6a7357dbcd65aa6
Source dataset
uspto-grants-2002_07
Patent number
US06420426B1

Reaction notes

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