Ethanol → Ethyl 4-formyl-2-methylbenzoate

HRID 1504610Notes

Reaction equation

HRID 1504610 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 H2O. 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 H2O
  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-f4eb3c46323649e196a2d582c43e9732
Source dataset
uspto-grants-2015_12
Patent number
US09215870B2

Reaction notes

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