Sodium Hydroxide → 3-(3-Methoxypropoxy)-4-methylbenzoic acid

HRID 1158404Notes

Reaction equation

HRID 1158404 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([O:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[CH:5]=1.[OH-].[Na+]>CCO>[CH3:16][O:15][CH2:14][CH2:13][CH2:12][O:11][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[CH3:10])[C:3]([OH:17])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68447108Methyl 3-(3-methoxypropoxy)-4-methylbenzoate

Product 1

HCID 573555373-(3-Methoxypropoxy)-4-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(3-methoxy-propoxy)-4-methyl-benzoic acid methyl ester (7.12 g, 32.86 mmol) and NaOH (1 N in water, 100 mL, 100 mmol) in EtOH (100 mL) is refluxed for 1 h. The reaction mixture is allowed to reach RT, and the solvent is concentrated under reduced pressure. The residue is dissolved in water (200 mL) and washed with ether (50 mL×3). The pH is adjusted to 2 by addition of cc HCl and the aqueous layer extracted with AcOEt (150 mL×2). The combined organic extracts are dried over Na2SO4, filtered and concentrated in vacuo. The crude material is recrystallized in diethyl ether/hexane to afford the desired title product. TLC, Rf (hexane/AcOEt 2:1)=0.15. MS (LC-MS): 224.0 [M−H]+. 1H-NMR (CDCl3, 300 MHz): δ=2.10 (p, 2H), 2.3 (s, 3H), 3.38 (s, 3H), 3.62 (t, 2H), 4.15 (t, 2H), 7.2 (d, 1H), 7.55 (s, 1H), 7.65 (d, 1H) ppm.

Workup

  1. customto reach RT
  2. concentrationthe solvent is concentrated under reduced pressure
  3. dissolutionThe residue is dissolved in water (200 mL)
  4. washwashed with ether (50 mL×3)
  5. additionThe pH is adjusted to 2 by addition of cc HCl
  6. extractionthe aqueous layer extracted with AcOEt (150 mL×2)
  7. dry with materialThe combined organic extracts are dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude material is recrystallized in diethyl ether/hexane

Sources & evidence

ORD record
ord-6ef41fb171304d6c80c10c8538ff5e49
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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