Methanol → Methyl 3-Hydroxyphenylacetate

HRID 1017557Notes

Reaction equation

HRID 1017557 reaction equation
S(Cl)(Cl)=O.[OH:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([OH:15])=[O:14])[CH:9]=[CH:10][CH:11]=1.[CH3:16]O>>[OH:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 121223'-Hydroxyphenylacetic acidHCID 24386Thionyl Chloride

Product 1

HCID 39129Methyl 3-HydroxyphenylacetateYield 94%

Conditions

Temperature
0 °C

Procedure

Thionyl chloride (17 mL, 0.64 mol) was added dropwise to methanol at 0° C. After the completion of the addition, the reaction mixture was stirred at 0° C. for 10 min., and then 3-hydroxyphenylacetic acid (25 g, 0.16 mol) was added. The resulting reaction mixture was stirred at room temperature for 2 h. Volatiles were removed and the residue was partitioned between water and ethyl acetate. The organic layer was separated, washed with H2O, NaHCO3, and NaCl (sat.) and dried over Na2SO4. The crude product was purified on a silica gel column with 20% EtOAc in hexane to give methyl 3-hydroxyphenylacetate as a colorless oil (25 g, 94% yield).

Workup

  1. additionAfter the completion of the addition
  2. customThe resulting reaction mixture
  3. stirringwas stirred at room temperature for 2 h
  4. customVolatiles were removed
  5. customthe residue was partitioned between water and ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with H2O, NaHCO3, and NaCl (sat.)
  8. dry with materialdried over Na2SO4
  9. customThe crude product was purified on a silica gel column with 20% EtOAc in hexane

Sources & evidence

ORD record
ord-70b7db2a0d7b4ec5a667c343b7be97f4
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

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