Methanol → Methyl alpha-methylbenzeneacetate

HRID 485955

Reaction equation

HRID 485955 reaction equation
[C:1]1([CH:7]([CH3:11])[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:12]O>OS(O)(=O)=O>[C:1]1([CH:7]([CH3:11])[C:8]([O:10][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 102962-Phenylpropionic acid

Product 1

HCID 569653Methyl alpha-methylbenzeneacetate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2-Phenylpropionic acid (8.4 g, 56 mmol) in methanol (180 ml) and concentrated H2SO4 (2 ml) were heated at reflux for 4 hours. The reaction was cooled down to room temperature and concentrated in vacuo (~30 ml), which was poured into ice water (~100 ml). The products were extracted with Et2O (150 ml×3), which was washed with saturated NaHCO3, H2O and dried over MgSO4. Filtration and evaporation of solvent yielded a yellow oil (8.9 g), which was distilled to give a colorless oil (8.34 g, 51 mmol, 91%, b.p. 73° C./1.5 mm Hg).

Workup

  1. temperatureat reflux for 4 hours
  2. concentrationconcentrated in vacuo (~30 ml), which
  3. additionwas poured into ice water (~100 ml)
  4. extractionThe products were extracted with Et2O (150 ml×3), which
  5. washwas washed with saturated NaHCO3, H2O
  6. dry with materialdried over MgSO4
  7. filtrationFiltration and evaporation of solvent

Sources & evidence

ORD record
ord-06ed26d513e7433cb5662eeb41bbaf6e
Source dataset
uspto-grants-1985_08
Patent number
US04537981

Linked notes

Loading…