Methanol → p-Hydroxyphenylglycine methyl ester

HRID 1976431

Reaction equation

HRID 1976431 reaction equation
S(Cl)(Cl)=O.[CH:5]1[C:10]([C@@H:11]([NH2:15])[C:12]([OH:14])=[O:13])=[CH:9][CH:8]=[C:7]([OH:16])[CH:6]=1.[CH3:17]O>>[CH3:17][O:13][C:12](=[O:14])[CH:11]([NH2:15])[C:10]1[CH:9]=[CH:8][C:7]([OH:16])=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 89853D-p-hydroxyphenylglycine

Product 1

HCID 4123006p-Hydroxyphenylglycine methyl ester

Procedure

To 50 mL of methanol cooled to 0° C. was dropwise added 3.75 mL of thionyl chloride foolowed by 5.0 g (0.030 mmol) of D-4-hydroxyphenylglycine. The reaction was heated to reflux for 5 h then stirred overnight at room temperature. The resulting mixture was concentrated in vacuo and the residue was diluted with ether. The resulting solid was collected by filtration and dried in vacuo to provide 5.9 g of amino-(4-hydroxy-phenyl)-acetic acid methyl ester as a white solid. Electrospray Mass Spec 182.2 (M+H)+

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 5 h
  3. concentrationThe resulting mixture was concentrated in vacuo
  4. additionthe residue was diluted with ether
  5. filtrationThe resulting solid was collected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-5206de63ecb2439687b0e75267bee4f1
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Linked notes

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