Ethanol → Ethyl 4-formylbenzoate

HRID 345109Notes

Reaction equation

HRID 345109 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=[O:2].[CH3:12][CH2:13]O.CCOCC>ClCCCl>[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH2:12][CH3:13])=[O:8])=[CH:5][CH:4]=1)=[O:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 3283Diethyl EtherHCID 120884-Formylbenzoic acid

Product 1

HCID 80498Ethyl 4-formylbenzoateYield 68%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4-formylbenzoic acid (25 g) conc sulfuric acid (2 ml) and EtOH (19.5 ml) was refluxed gently for 5 days in 100 ml of 1,2-dichloroethane. The solvent was then stripped, and Et2O was added to the residue. The Et2O solution was washed (satd aq NaHCO3) dried (Na2SO4), filtered, and evaporated. Bulb to bulb distillation afforded 20.1 g (68%) of the title ester as a clear liquid, bp 145°-150° (2,900 Pascals, 22 torr).

Workup

  1. washThe Et2O solution was washed (satd aq NaHCO3)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. distillationBulb to bulb distillation

Sources & evidence

ORD record
ord-5635fc28c9b1430caea087668a77e35f
Source dataset
uspto-grants-1991_10
Patent number
US05055450

Reaction notes

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