Ethanol → Ethyl 4-chlorobenzoylformate

HRID 1720848Notes

Reaction equation

HRID 1720848 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([C:8]#N)=[O:7])=[CH:4][CH:3]=1.[Br-].[Na+].S(=O)(=O)(O)[OH:15].[CH2:19]([OH:21])[CH3:20]>O>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[O:7])[C:8]([O:21][CH2:19][CH3:20])=[O:15])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 253881Sodium BromideHCID 98340514-Chlorobenzoyl cyanide

Product 1

HCID 2758815Ethyl 4-chlorobenzoylformateYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Chlorobenzoyl cyanide (13.0 g, 0.079 mol) prepared in Example 1a was added to a stirred mixture of sodium bromide (1.0 g, 0.01 mol) and 80% sulphuric acid (10 ml). An exothermic reaction took place with the formation of a solid yellow mass. Ethanol (50 ml) was added and the mixture was heated under reflux to give a yellow solution. On cooling, a colourless precipitate formed. The mixture was diluted with cold water and extracted with isopropyl ether. The organic extract was washed with water, sodium bicarbonate solution and then again with water and dried over sodium sulphate. Evaporation and distillation of the solution gave the product as a yellow oil (8.2 g, 54%)--b.p. 82°-84° C./0.05 mm Hg.

Workup

  1. customAn exothermic reaction
  2. temperaturethe mixture was heated
  3. temperatureunder reflux
  4. customto give a yellow solution
  5. temperatureOn cooling
  6. customa colourless precipitate formed
  7. extractionextracted with isopropyl ether
  8. extractionThe organic extract
  9. washwas washed with water, sodium bicarbonate solution
  10. dry with materialagain with water and dried over sodium sulphate
  11. customEvaporation and distillation of the solution

Sources & evidence

ORD record
ord-b4dbe0ba9bf548d0b22be7dbf59215aa
Source dataset
uspto-grants-1996_04
Patent number
US05508251

Reaction notes

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