Ethanol → Ethyl 4-formyl-2-methylbenzoate

HRID 1502937Notes

Reaction equation

HRID 1502937 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([CH3:12])[CH:4]=1)=[O:2].S(=O)(=O)(O)O.[CH2:18](O)[CH3:19]>>[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH2:18][CH3:19])=[O:8])=[C:5]([CH3:12])[CH:4]=1)=[O:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 207748714-Formyl-2-methylbenzoic acid

Product 1

HCID 20543014Ethyl 4-formyl-2-methylbenzoateYield 80%

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 4-formyl-2-methylbenzoic acid (3 g, 18.2 mmol) in ethyl alcohol (EtOH; 30 mL) was added sulfuric acid (H2SO4, x M; 2 mL), and the reaction mixture was heated at 80° C. for 18 h. The reaction mixture was cooled to 25° C. and concentrated under reduced pressure. The residue was diluted with EtOAc and washed with water. The combined EtOAc extracts were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford the title compound as a solid (2.8 g, 80%): 1H NMR (400 MHz, CDCl3) δ 10.05 (s, 1H), 8.04 (m, 1H), 7.75 (m, 2H), 4.43 (m, 2H), 2.65 (s, 3H), 1.42 (m, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to 25° C.
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with EtOAc
  4. washwashed with water
  5. washThe combined EtOAc extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-024a2bcfc7f449b7aec67de2c916b329
Source dataset
uspto-grants-2015_12
Patent number
US09211281B2

Reaction notes

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