Benzenepropanoic acid → Methyl 3-phenylpropionate

HRID 2226816Notes

Reaction equation

HRID 2226816 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[CH3:17]O>>[C:1]1([CH2:7][CH2:8][C:9]([O:11][CH3:17])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 107Benzenepropanoic acidHCID 887MethanolHCID 1118Sulfuric Acid

Product 1

HCID 7643Methyl 3-phenylpropionate

Procedure

A solution of 3-phenylpropionic acid (50 g, 0.33 mole) and conc. sulfuric acid (5 g) in methanol (220 ml) was refluxed for 1 hour with the stirring, concentrated and poured into cold H2O. The mixture was extracted with methylene chloride (75 ml×3), the organic layer was washed with H2O (125 ml×2), dried over anhydrous MgSO4 and evaporated. The residue (54 g) was distilled under reduced pressure to give 51.5 g of methyl 3-phenylpropionate as a colorless oil.

Workup

  1. concentrationconcentrated
  2. additionpoured into cold H2O
  3. extractionThe mixture was extracted with methylene chloride (75 ml×3)
  4. washthe organic layer was washed with H2O (125 ml×2)
  5. dry with materialdried over anhydrous MgSO4
  6. customevaporated
  7. distillationThe residue (54 g) was distilled under reduced pressure

Sources & evidence

ORD record
ord-f88ad4b0719c4d63a258a7fd927d5f1e
Source dataset
uspto-grants-1994_09
Patent number
US05350660

Reaction notes

Loading…