2,5-Dimethylbenzoic acid → Methyl 2,5-dimethylbenzoate

HRID 2361329

Reaction equation

HRID 2361329 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.O1CCOC[CH2:14]1>>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([O:6][CH3:14])=[O:5]

Participants

3

Reactant 2

HCID 118922,5-Dimethylbenzoic acidHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 273300Methyl 2,5-dimethylbenzoateYield 82.4%

Procedure

A colorless, homogeneous solution of 2,5-dimethylbenzoic acid (6.3264 g, 42.1 mmol) and 4 N HCl/1,4-dioxane (11.58 mL, 46.3 mmol) was refluxed under nitrogen. After 2.5 hr, the reaction was cooled to room temperature and concentrated in vacuo. The residue was dissolved in EtOAc (100 mL) and washed with water (40 mL), 1N aq. NaOH (40 mL), water (40 mL) and brine (40 mL), successively. The organic solution was dried over MgSO4 and concentrated in vacuo to give the desired product (5.934 g, 34.7 mmol, 82% yield) as a colorless oil.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc (100 mL)
  3. washwashed with water (40 mL), 1N aq. NaOH (40 mL), water (40 mL) and brine (40 mL)
  4. dry with materialThe organic solution was dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dca110198fd24d218f488171ec343e3b
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Linked notes

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