Water → Methyl 3-methoxy-5-(3-methoxypropoxy)benzoate

HRID 1698355Notes

Reaction equation

HRID 1698355 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([O:11][CH3:12])[CH:5]=1.[CH3:14][O:15][CH2:16][CH2:17]COS(C1C=CC(C)=CC=1)(=O)=O.[C:30]([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:5]=[C:6]([O:11][CH2:12][CH2:17][CH2:16][O:15][CH3:14])[CH:7]=[C:8]([O:10][CH3:30])[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 135229883-Methoxypropyl 4-methylbenzenesulfonateHCID 13941268Methyl 3-hydroxy-5-methoxybenzoate

Product 1

HCID 59817706Methyl 3-methoxy-5-(3-methoxypropoxy)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 3-methoxy-5-hydroxybenzoic acid methyl ester (23.2 g, 127 mmol), toluene-4-sulfonic acid 3-methoxy-propyl ester (40.7 g, 167 mmol) and Kl (2.23 g, 13.4 mmol) in DMF (350 mL), K2CO3 (53.1 g, 384 mmol) is added under N2. After stirring at 60° C. for 17 h, the reaction mixture is supplemented with H2O and extracted with Et2O. The combined organic phases are washed with H2O and dried (Na2SO4). Concentration under reduced pressure and silica gel flash chromatography give the title compound as colorless oil. MS: 255 [M+H]+; tR (HPLC, CombiScreen ODS-AM 50×4.6 mm; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 5 min then 100% CH3CN+0.1% TFA for 2 min, flow 2.0 ml/min): 3.80 min.

Workup

  1. extractionextracted with Et2O
  2. washThe combined organic phases are washed with H2O
  3. dry with materialdried (Na2SO4)
  4. concentrationConcentration under reduced pressure and silica gel flash chromatography

Sources & evidence

ORD record
ord-56802f60222348b68277d2f96277ad75
Source dataset
uspto-grants-2012_04
Patent number
US08163773B2

Reaction notes

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