Ethanol → Ethyl 2,4-dimethylbenzoate

HRID 1907038Notes

Reaction equation

HRID 1907038 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[OH-].[Ca+2].[OH-].[CH2:20](O)[CH3:21]>>[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:20][CH3:21])=[O:5]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 118972,4-Dimethylbenzoic acidHCID 6093208Calcium Hydroxide

Product 1

HCID 118492Ethyl 2,4-dimethylbenzoateYield 95%

Procedure

To a solution of commercially available 2,4-dimethylbenzoic acid (67.8 g, 451 mmol) in 1000 mL of ethanol was added 10 mL of sulfuric acid. The mixture was refluxed over night, cooled down and was neutralized by adding calcium hydroxide in small portions (˜30 g). The suspension was filtered over celite and concentrated in vacuo. The crude product was purified by vacuum distillation yielding 76.4 g (95%) of 1 as a colorless oil: 1H-NMR (400 MHz, CDCl3): δ 1.38 (t, J=7.3 Hz, 3H), 2.34 (s, 3H), 2.57 (s, 3H), 4.33 (q, J=7.2 Hz, 2H), 7.01-7.06 (m, 2H), 7.82 (d, J=8.5 Hz, 1H); 13C-NMR (100 MHz, CDCl3): δ 14.3, 21.3, 21.7, 60.4, 126.3, 126.9, 130.7, 132.4, 140.1, 142.3, 167.6; MS (ESI) m/z=133.0 (100), 132.0 (57), 178.1 (M+, 51).

Workup

  1. temperatureThe mixture was refluxed over night
  2. temperaturecooled down
  3. filtrationThe suspension was filtered over celite and
  4. concentrationconcentrated in vacuo
  5. distillationThe crude product was purified by vacuum distillation

Sources & evidence

ORD record
ord-2be7d153eea24d71a5c612c88a56299c
Source dataset
uspto-grants-2013_12
Patent number
US08597631B2

Reaction notes

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