Water → HCID 53900511, compound

HRID 2398491Notes

Reaction equation

HRID 2398491 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([CH2:10][CH3:11])[C:7]([OH:12])=[C:6]([CH2:13][CH3:14])[CH:5]=1.[OH-].[Na+].O.S(OC)(O[CH3:23])(=O)=O>CCOCC>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([CH2:10][CH3:11])[C:7]([O:12][CH3:23])=[C:6]([CH2:13][CH3:14])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 541130503,5-Diethyl-4-hydroxybenzoic acid methyl ester

Product 1

HCID 53900511HCID 53900511, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a cooled solution of 16.2 (0.078 mol.) of 3,5-diethyl-4-hydroxybenzoic acid methyl ester and 4.0 g. (0.1 mol.) of sodium hydroxide in 100 ml. of water is added 9.8 g. (7.3 ml., 0.079 mol.) of dimethyl sulfate. The reaction mixture is refluxed for two hours. After cooling, ether is added and the layers are separated. The organic phase is washed with water, dilute sulfuric acid and water, dried (Na2SO4) and concentrated to give 3,5-diethyl-4-methoxybenzoic acid methyl ester.

Workup

  1. temperatureThe reaction mixture is refluxed for two hours
  2. temperatureAfter cooling
  3. customthe layers are separated
  4. washThe organic phase is washed with water, dilute sulfuric acid and water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-36b55108f3424d2ebee0f6e3ef599961
Source dataset
uspto-grants-1977_05
Patent number
US04024273

Reaction notes

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