Methylparaben → 4-(2-Chloro-ethoxy)-benzoic acid methyl ester

HRID 1032680Notes

Reaction equation

HRID 1032680 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C1(S(O[CH2:22][CH2:23][Cl:24])(=O)=O)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)CC(=O)C>[Cl:24][CH2:23][CH2:22][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 136344852-Chloroethyl Benzenesulfonate

Product 1

HCID 64854314-(2-Chloro-ethoxy)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of methyl 4-hydroxybenzoate (15.2 g, 0.1 M), 2-(benzenesulphonyloxy)ethyl chloride (28.65 g, 0.12 M) and potassium carbonate (19.15 g, 0.1 M) in 4-methylpentan-2-one (170 ml) was stirred at reflux for 24 hours. After cooling, distilled water (170 ml) was added and the organic phase separated off. Evaporation to dryness gave a yellow solid which was crystallised from ethanol to give the title compound, yield (13.3 g), m.p. 56°-58°.

Workup

  1. temperatureat reflux for 24 hours
  2. temperatureAfter cooling
  3. distillationdistilled water (170 ml)
  4. additionwas added
  5. customthe organic phase separated off
  6. customEvaporation to dryness
  7. customgave a yellow solid which
  8. customwas crystallised from ethanol

Sources & evidence

ORD record
ord-155dd5b9705d440088435f1c5e49d8f2
Source dataset
uspto-grants-1990_09
Patent number
US04959366

Reaction notes

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