Sodium Hydroxide → 4-Isopropoxy-3-(methoxymethyl)benzoic acid

HRID 219864Notes

Reaction equation

HRID 219864 reaction equation
[CH:1]([O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[CH:7][C:6]=1[CH2:15][O:16][CH3:17])([CH3:3])[CH3:2].[OH-].[Na+]>CCO.O>[CH:1]([O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[CH2:15][O:16][CH3:17])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67529014Methyl 4-isopropoxy-3-(methoxymethyl)benzoate

Product 1

HCID 594957854-Isopropoxy-3-(methoxymethyl)benzoic acidYield 91.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl 4-isopropoxy-3-(methoxymethyl)benzoate (11.30 g; 47.42 mmol; 1 eq.) in EtOH (339 mL) at RT was treated with NaOH (47.42 mL; 5 M; 237.11 mmol; 5 eq.). The reaction mixture was stirred at RT for 12 hours. The reaction mixture was concentrated to give a yellow solid. It was taken up in water and the aqueous phase was washed with EtOAc and then acidified with HCl cc to pH 2. The aqueous layer was extracted with EtOAc (twice). The combined organics were washed with brine, dried over MgSO4 and concentrated affording the title compound as a beige solid (9.71 g, 91%). 1H NMR (DMSO-d6, 300 MHz) δ 12.39 (br s, 1H), 7.89-7.82 (m, 2H), 7.11-7.07 (d, J=8.75 Hz, 1H), 4.79-4.67 (sept, J=5.92 Hz, 1H), 4.39 (s, 2H), 3.35 (s, 3H), 1.31-1.28 (d, J=6.06 Hz, 6H). LC/MS (Method B): 223.2 (M−H)−. HPLC (Method A) Rt 3.71 min (Purity: 92.8%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give a yellow solid
  3. washthe aqueous phase was washed with EtOAc
  4. extractionThe aqueous layer was extracted with EtOAc (twice)
  5. washThe combined organics were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-34a315adb0a9408b92dc6122ebd404be
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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