Sodium Methoxide → HCID 86735825, compound

HRID 261294Notes

Reaction equation

HRID 261294 reaction equation
Br[CH2:2][C:3]1[C:4]([C:10]([O:12][CH2:13]C)=[O:11])=[CH:5][C:6]([Cl:9])=[CH:7][CH:8]=1.[CH3:15][O-:16].[Na+]>CO>[CH3:13][O:12][C:10]([C:4]1[C:3]([CH2:2][O:16][CH3:15])=[CH:8][CH:7]=[C:6]([Cl:9])[CH:5]=1)=[O:11]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 13272463Ethyl 2-(bromomethyl)-5-chlorobenzoate

Product 1

HCID 86735825HCID 86735825, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl α-Bromo-4-chloro-o-toluate (26.4 g.) is added to a solution (10°) of sodium methoxide (5.4 g.) in 110 ml. of methanol. When the addition is complete, the mixture is refluxed for two hours, then cooled and concentrated in vacuo. The oily residue is partioned between ether-water. The ether layer is separated and dried. Removal of the drying agent and concentration of the filtrate in vacuo leaves 17.3 g. of a white solid. A sample of the product recrystallized from methanol had mp 44°-45°.

Workup

  1. additionWhen the addition
  2. temperaturethe mixture is refluxed for two hours
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customThe ether layer is separated
  6. customdried
  7. customRemoval of the drying agent and concentration of the filtrate in vacuo
  8. customleaves 17.3 g
  9. customA sample of the product recrystallized from methanol

Sources & evidence

ORD record
ord-e81d66817ce3492c9eb2ca08ded3fc73
Source dataset
uspto-grants-1979_08
Patent number
US04165231

Reaction notes

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