Methanol → HCID 117759835, compound

HRID 709714Notes

Reaction equation

HRID 709714 reaction equation
[OH:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.[CH3:19]O>>[OH:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([CH2:8][CH2:9][C:10]([O:12][CH3:19])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 84733342HCID 84733342, compound

Product 1

HCID 117759835HCID 117759835, compound

Procedure

To a solution of 3-(3-hydroxy-2-methoxyphenyl)propanoic acid (50 mg) in methanol (10 mL) was added dropwise thionyl chloride (2.0 mL) at 0° C. The reaction mixture was heated under reflux for 3 hr. The reaction mixture was concentrated, and ethyl acetate was added. The reaction mixture was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (45 mg) as a yellow oil. This compound was used for the next step without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 hr
  3. concentrationThe reaction mixture was concentrated
  4. additionethyl acetate was added
  5. washThe reaction mixture was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4872e1c2cf97447bb5db224bc2251390
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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