Water → Ethyl anisate

HRID 2303440Notes

Reaction equation

HRID 2303440 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[OH-].[K+].O.S(OC)(O[CH3:20])(=O)=O>C(OCC)C>[CH3:20][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 8434EthylparabenHCID 14797Potassium Hydroxide

Product 1

HCID 60979Ethyl anisate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl 4-hydroxybenzoate (15.0 g, 0.09 mol) is stirred into an initial mixture of KOH (6.3 g, 0.11 mol) in dist. water (60 ml) under protective gas. Dimethyl sulfate (8.8 ml, 0.09 mol) is added dropwise to the clear solution with stirring and ice-cooling such that the temperature does not exceed 15° C. After addition is complete, the cooling is removed, and to complete the reaction the reaction mixture is stirred at RT for 45 min and under reflux for 2 h, then cooled to RT. The deposited oil is taken up in diethyl ether (50 ml). The aqueous phase separated off is extracted with diethyl ether (150 ml), and the ethereal extracts obtained are combined, washed with sodium hydroxide solution (10% strength, 50 ml) and with saturated NaCl solution, dried over Na2SO4 sicc. and concentrated in vacuo: colorless oil, yield: 15.7 g (97%).

Workup

  1. temperatureice-cooling such that the temperature
  2. customdoes not exceed 15° C
  3. additionAfter addition
  4. customthe cooling is removed
  5. customthe reaction the reaction mixture
  6. stirringis stirred at RT for 45 min
  7. temperatureunder reflux for 2 h
  8. customThe aqueous phase separated off
  9. extractionis extracted with diethyl ether (150 ml)
  10. customthe ethereal extracts obtained
  11. washwashed with sodium hydroxide solution (10% strength, 50 ml) and with saturated NaCl solution
  12. dry with materialdried over Na2SO4 sicc
  13. concentrationand concentrated in vacuo

Sources & evidence

ORD record
ord-531cebebf9314164afc9e589851a7d84
Source dataset
uspto-grants-2002_08
Patent number
US06432988B1

Reaction notes

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