Water → HCID 53900511, compound

HRID 268391Notes

Reaction equation

HRID 268391 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 g. (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 2 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 2 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-f9fa7b4dbd8b424b97fef61656888c76
Source dataset
uspto-grants-1976_03
Patent number
US03947470

Reaction notes

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