Benzoic Acid → Methyl Benzoate

HRID 273659Notes

Reaction equation

HRID 273659 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10]O.S(=O)(=O)(O)O>>[C:1]([O:9][CH3:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 243Benzoic AcidHCID 887MethanolHCID 1118Sulfuric Acid

Product 1

HCID 7150Methyl BenzoateYield 56%

Procedure

A solution of benzoic acid (30 g; 0.25 mole in MeOH (80 g; 2.5 mole) and conc. sulphuric acid (2.7 ml) was passed through the CMR (10.5 ml/min.; 141°-5° C.; 760 kPa). Excess MeOH was removed by rotary evaporation and the residue poured into water (250 ml) and the product extracted in CCl4. The organic phase was washed with bicarbonate solution, dried over MgSO4, filtered, evaporated, and the product (18.6 g; 56% yield) distilled under reduced pressure; b.p. 109° C./30 mm of Hg. cf ref.3, where a different method of work-up was used, and a yield of 92% was obtained after 4 hours at reflux.

Workup

  1. customwas passed through the CMR (10.5 ml/min.; 141°-5° C.; 760 kPa)
  2. customExcess MeOH was removed by rotary evaporation
  3. additionthe residue poured into water (250 ml)
  4. extractionthe product extracted in CCl4
  5. washThe organic phase was washed with bicarbonate solution
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. distillationthe product (18.6 g; 56% yield) distilled under reduced pressure
  10. customa yield of 92% was obtained after 4 hours
  11. temperatureat reflux

Sources & evidence

ORD record
ord-099cac496dd8462b814d29809563538d
Source dataset
uspto-grants-1995_02
Patent number
US05387397

Reaction notes

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