Methanol → Methyl 3-Hydroxyphenylacetate

HRID 1969016Notes

Reaction equation

HRID 1969016 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.[CH3:16]O>>[CH3:16][O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 121223'-Hydroxyphenylacetic acidHCID 24386Thionyl Chloride

Product 1

HCID 39129Methyl 3-Hydroxyphenylacetate

Procedure

To 3-hydroxyphenylacetic acid (5.07 g, 33.32 mmol) in MeOH (50 mL) was added thionyl chloride (4.85 mL, 66.65 mmol) dropwise over 30 minutes by addition funnel. Once no starting material was seen by analytical LCMS, the mixture was concentrated, and the residue was partitioned between EtOAc and 1N aqueous NaOH. The aqueous layer was extracted twice with EtOAc, and the combined organic layers were dried and concentrated to give the title compound.

Workup

  1. additionby addition funnel
  2. concentrationthe mixture was concentrated
  3. customthe residue was partitioned between EtOAc and 1N aqueous NaOH
  4. extractionThe aqueous layer was extracted twice with EtOAc
  5. customthe combined organic layers were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-614d3b1d6364480f833f86ccc717b522
Source dataset
uspto-grants-2013_04
Patent number
US08426449B2

Reaction notes

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