Hydrochloric Acid → HCID 5080667, compound

HRID 457962Notes

Reaction equation

HRID 457962 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 C10H10O4: 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-4fccc62dcdc44d689a804160a9dd2af7
Source dataset
uspto-grants-2007_03
Patent number
US07189749B2

Reaction notes

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