Benzenepropanoic acid → Methyl 3-phenylpropionate

HRID 1378900Notes

Reaction equation

HRID 1378900 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 stirring, concentrated and poured into cold H2O. The mixture was extracted thrice with methylene chloride (75 ml), the organic layer was washed thrice with H2O (125 ml), dried over anhydrous MgSO4 and evaporated. The residual crude oil (54 g) was distilled under reduced pressure to give 51.5 g of methyl 3-phenylpropionate as a colorless oil having a boiling point of 94°-95° C.B 5 mmHg.

Workup

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

Sources & evidence

ORD record
ord-51ec3d88b341447b8f99f5433034a3af
Source dataset
uspto-grants-1997_09
Patent number
US05670299

Reaction notes

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