Sodium Methoxide → HCID 86735825, compound

HRID 866355Notes

Reaction equation

HRID 866355 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-3a290d7836084c9f8dfae0b7fc76a79e
Source dataset
uspto-grants-1978_07
Patent number
US04098812

Reaction notes

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