Methanol → Methyl 3-phenoxypropionate

HRID 1941902Notes

Reaction equation

HRID 1941902 reaction equation
[O:1]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:13]O>OS(O)(=O)=O>[O:1]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 815963-Phenoxypropionic acid

Product 1

HCID 347927Methyl 3-phenoxypropionateYield 92.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

3-phenoxypropionic acid (5.0 g, 30 mmol) was dissolved in MeOH (12 mL) and H2SO4 (18 M, 3 drops) was added. The mixture was place in the microwave reactor (T: 140° C., t: 5 min). The solvent was evaporated, the mixture was partitioned in EtOAc (30 mL) and NaOH (2N, 20 mL). The organic phase was dried over MgSO4, filtered, and evaporated to give methyl 3-phenoxypropanoate (5.0 g, 27.7 mmol, 92.5%).

Workup

  1. customin the microwave reactor (T: 140° C., t: 5 min)
  2. customThe solvent was evaporated
  3. customthe mixture was partitioned in EtOAc (30 mL)
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-a63e625b02f84da18c54bd5e41dcbc63
Source dataset
uspto-grants-2013_03
Patent number
US08389517B2

Reaction notes

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