Sodium Hydroxide → 3-Methyl-4-(methylsulfonyl)benzoic acid

HRID 72982Notes

Reaction equation

HRID 72982 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[S:12]([CH3:15])(=[O:14])=[O:13])[C:5]([O:7]C)=[O:6].[OH-].[Na+]>O1CCOCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[S:12]([CH3:15])(=[O:14])=[O:13])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53429641HCID 53429641, compound

Product 1

HCID 534295973-Methyl-4-(methylsulfonyl)benzoic acidYield 97.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of methyl 3-methyl-4-methylsulfonyl-benzoate (5.8 g, 25.4 mmol) in dioxane (25 mL) was added NaOH (20 g, 125.0 mmol) (aq. 25%) and the reaction mixture was heated at 75° C. for 1 hour. The reaction mixture was cooled and was concentrated in vacuo to half the volume and adjusted to pH 2 with 6N HCl solution. The aqueous layer was extracted with ethyl acetate (3×100 mL). The organics were washed with brine solution (50 mL), dried over MgSO4 and concentrated in vacuo to give 3-methyl-4-methylsulfonyl-benzoic acid (5.3 g, 97%) as a white solid. ESI-MS m/z calc. 214.5. Found 215.5 (M+1)+; Retention time: 0.67 minutes (3 min run); 1H NMR (400 MHz, DMSO) δ 13.48 (s, 1H), 8.13-7.81 (m, 3H), 3.33 (s, 3H), 2.70 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationwas concentrated in vacuo to half the volume
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×100 mL)
  4. washThe organics were washed with brine solution (50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-91d9b1e9c1694d4e86c47ecf91389d44
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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