Sodium Methoxide → Ethyl 3-(5-hydroxy-2-methoxyphenyl)propanoate

HRID 709696Notes

Reaction equation

HRID 709696 reaction equation
C[O-].[Na+].[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12]C(OC)=O)=[CH:8][C:7]=1[CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CO>[OH:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH3:4])=[C:7]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 117759608Ethyl 3-(2-methoxy-5-(methoxycarbonyloxy)phenyl)propanoate

Product 1

HCID 69644523Ethyl 3-(5-hydroxy-2-methoxyphenyl)propanoateYield 91.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of sodium methoxide (227 mg) in methanol (10 ml) was added ethyl 3-(2-methoxy-5-(methoxycarbonyloxy)phenyl)propanoate (1.00 g), and the mixture was stirred for 1 hr. The reaction mixture was concentrated, and the residue was extracted with ethyl acetate. The extract was washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (730 mg) as a yellow oil. This compound was used for the next step without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c209110839de406ba4a2c99eacf1366a
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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